Nitromethane → HCID 9888784, compound

HRID 988009Notes

Reaction equation

HRID 988009 reaction equation
[O:1]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:12]=[O:13])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[N+:25]([CH3:28])([O-:27])=[O:26]>C1COCC1>[O:1]([C:9]1[CH:10]=[C:11]([C@@H:12]([OH:13])[CH2:28][N+:25]([O-:27])=[O:26])[CH:14]=[CH:15][C:16]=1[O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:20])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6375NitromethaneHCID 109374483,4-di(t-butyldimethylsiloxy)benzaldehyde

Product 1

HCID 9888784HCID 9888784, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

105 mg (0.28 mmol) of 3,4-di(t-butyldimethylsiloxy)benzaldehyde was dissolved in 10 ml of THF under the atmosphere of argon at −40° C., and 0.31 ml of rare earth metal complex solution D1 was mixed into the solution. After stirring for 30 minutes, 85.5 mg (1.40mmol) of nitromethane was added dropwise to the mixture. After 61-hour reaction time, (R)-1-(3,4-di(t-butyldimethylsilxy)phenyl)-2-nitroethanol with an optical purity of 87% e.e. was obtained in a yield of 86%.

Workup

  1. customwas obtained in a yield of 86%

Sources & evidence

ORD record
ord-27ddb4b3f2fa4b5591d7c688db2a325c
Source dataset
uspto-grants-2003_10
Patent number
US06632955B1

Reaction notes

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