2-Phenylethanol → 2-Phenylethyl cyanoacetate

HRID 973445Notes

Reaction equation

[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][OH:9])=[CH:3][CH:2]=1.[C:10]([CH2:12][C:13](O)=[O:14])#[N:11]>CN(C=O)C.CN(C)C1C=CN=CC=1>[C:10]([CH2:12][C:13]([O:9][CH2:8][CH2:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)=[O:14])#[N:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of β-phenethyl alcohol (3.6 ml, 30.0 mmol) in DMF (30 ml) was added cyanoacetic acid (2.55 g, 30.0 mmol) in DMF (20 ml) and the whole was cooled to 0° C. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimido (4.66 g, 30.0 mmol) in DMF (5 ml) and 4-dimethylaminopyridine (0.37 g, 3.0 mmol) in DMF (10 ml) were then added to the mixture in that order at 0° C. and stirring was continued for 1 hour at this temperature and 18 hours at room temperature. The reaction mixture was concentrated in vacuo and purified by column chromatography to afford phenethyl cyanoacetate (2.49 g, 13.2 mmol).

Workup

concentrationThe reaction mixture was concentrated in vacuo
custompurified by column chromatography

Sources & evidence

ORD record: ord-d44688fa6d6f467caeda7299acc07341
Source dataset: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05063243

Reaction notes

Loading…