(R)-(-)-Glycidyl-4-nitrobenzenesulfonate → (R)-2-Cyano-5-(3-carbethoxypropyl)phenyl Glycidyl Ether

HRID 1937779Notes

Reaction equation

HRID 1937779 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][C:4]=1[OH:17])#[N:2].S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:22][C@@H:23]1[O:25][CH2:24]1)(=O)=O>>[CH2:22]([O:17][C:4]1[CH:5]=[C:6]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][C:3]=1[C:1]#[N:2])[C@@H:23]1[O:25][CH2:24]1

Participants

3

Reactant 2

HCID 14292098(R)-(-)-Glycidyl-4-nitrobenzenesulfonateHCID 22461711Ethyl 4-(4-cyano-3-hydroxyphenyl)butanoate

Product 1

HCID 88171297(R)-2-Cyano-5-(3-carbethoxypropyl)phenyl Glycidyl EtherYield 89%

Procedure

Using the method of example 30(b), vide supra, ethyl 4-(4-cyano-3-hydroxyphenyl)butanoate (1.4 g, 6 mmol) and (R)-glycidyl nosylate (1.48 g, 5.71 mmol) were used to prepare 1.47 g (88%) of the title compound as a white solid.

Sources & evidence

ORD record
ord-afd2c80f22304125b502a4258019c311
Source dataset
uspto-grants-2002_05
Patent number
US06395919B1

Reaction notes

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