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

HRID 1937784Notes

Reaction equation

HRID 1937784 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=[CH:7][C:8]=1[OH:9])#[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:9][C:8]1[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][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 22461719Ethyl 4-(3-cyano-4-hydroxyphenyl)butanoate

Product 1

HCID 88171393(R)-2-cyano-4-(3-carbethoxypropyl)phenyl Glycidyl EtherYield 66.3%

Procedure

Using the method of example 30(b), supra, ethyl 4-(3-cyano-4-hydroxyphenyl)butanoate (0.93 g, 4 mmol) and (R)-glycidyl nosylate (1.00 g, 3.86 mmol) were used to prepare 0.74 g (66%) of the title compound as a white solid.

Sources & evidence

ORD record
ord-10cd4df174dd41129bd8c6dee2c5141a
Source dataset
uspto-grants-2002_05
Patent number
US06395919B1

Reaction notes

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