Ethyl 3-(4-cyano-3-hydroxyphenyl)propanoate → ethyl (R)-4-cyano-3-(oxiranylmethoxy)benzenepropionate

HRID 1937781Notes

Reaction equation

HRID 1937781 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][C:4]=1[OH:16])#[N:2].S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:21][C@@H:22]1[O:24][CH2:23]1)(=O)=O>>[CH2:21]([O:16][C:4]1[CH:5]=[C:6]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[CH:8][C:3]=1[C:1]#[N:2])[C@@H:22]1[O:24][CH2:23]1

Participants

3

Reactant 2

HCID 9834402Ethyl 3-(4-cyano-3-hydroxyphenyl)propanoateHCID 14292098(R)-(-)-Glycidyl-4-nitrobenzenesulfonate

Product 1

HCID 58700132ethyl (R)-4-cyano-3-(oxiranylmethoxy)benzenepropionateYield 86%

Procedure

Using the method of example 30(b), supra, ethyl 3-(4-cyano-3-hydroxyphenyl)propionate (1.32 g, 6 mmol) and (R)-glycidyl nosylate (1.48 g, 5.71 mmol) were used to prepare 1.35 g (86%) of the title compound as a white solid.

Sources & evidence

ORD record
ord-ade924d95d8d4d48ae019e668911e151
Source dataset
uspto-grants-2002_05
Patent number
US06395919B1

Reaction notes

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