All Notebooks | Help | Support | About
23rd April 2013 @ 01:09
Mnr: 21-30

As for Hydrolysis of MNR11-16 to MNR26-4 Hydrolysis of MNR11-17 to MNR26-5 Starting material from Synthesis of MNR11-18

Hazard and Risk Assessment:

HIRAC MNR7.pdf

Procedure:MNR11-8 (3.96 g, 10.63 mmol) was dissolved in EtOH (21 mL) and HCl (1M) (110 mL) and heated to reflux for 2.5 hours. The solution was allowed to cool to room temperature then cooled in an ice bath, basified with NaOH pellets (approx 8 g, pellets used to minimise volume of aqueous material) to pH 12-13 and extracted with DCM (4 x 100 mL). The organic fractions were combined, dried over magnesium sulphate, filtered and concentrated under reduced pressure to give an orange crispy solid (1.008 g).

TLCReaction mixture after 2.5 hours ran in 100% EtOAc

2013-04-23 13.15.20.jpg

IR 

5f rac IR MNR26-7.jpg

Strings Starting material InChI=1S/C21H28N2O4/c1-26-18-10-15-8-9-23-17(16(15)11-19(18)27-2)12-22(13-20(23)24)21(25)14-6-4-3-5-7-14/h10-11,14,17H,3-9,12-13H2,1-2H3 Product InChI=1S/C14H18N2O3/c1-18-12-5-9-3-4-16-11(7-15-8-14(16)17)10(9)6-13(12)19-2/h5-6,11,15H,3-4,7-8H2,1-2H3

Linked Entries
Attached Files
22nd March 2012 @ 06:12
Mnr: 21-30
Repeat of MNR21-3 on the same scale.

MNR21-3%20scheme.png

mnr21-3%20table.PNG

DOI: 10.1002/chem.201002046

Hazard and Risk Assessment:
HIRAC MNR23-3.pdf


Water (60 mL) was added to a 500 mL round-bottomed flask. Sodium hydroxide (60.0 g, 1.5 mol) was added portionwise followed by a mixture of 2-phenylethylamine (24.3 mL, 0.19 mol), chloroform (16.0 mL, 0.19 mol), and benzyltriethylammonium chloride (400 mg, 1.8 mmol) in dichloromethane (60 mL)dropwise over 10 mins. The reaction mixture was then refluxed for 4 hours.

The reaction mixture was then allowed to cool to room temperature and was diluted with ice and water (50 mL), the organic layer was separated and retained, the aqueous layer was extracted with DCM (2 x 60 mL). The organic fractions were then combined and washed with HCl (1M) (3 x 100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude as a dark orange oil (23.90 g) The crude was passed through a short column (60-100 EtOAC) collecting the top running spot. After concentration, (2-isocyanoethyl)benzene (MNR21-4) was afforded as a dark yellow oil (17.618 g, 134.31 mmol, 70%)

Characterisation

mnr21-4_1H.pdf
mnr21-4_frac1.zip


1H NMR (400 MHz, CDCl3): d = 7.37-7.21 (m, 5H), 3.60 (tt, J = 10.6, 1.9 Hz, 2H), 2.98 (tt, J = 10.6, 1.9 Hz, 2H)

13C NMR MW34-1


13C NMR – MW34-1 (50 MHz, CDCl3): d = 156.6, 136.7, 128.7, 128.7, 127.2, 42.9 (t, J = 6.5) 35.6.

IR MW34-1


Vmax/cm-1 2147, 1454

Preparation of 2-Phenylethyl isocyanide (MW34-1)

*lab book entry closed
Linked Posts
This post is linked by:
Attached Files