Hydrochloric Acid → HCID 9888784, compound

HRID 988007Notes

Reaction equation

HRID 988007 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].Cl>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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 109374483,4-di(t-butyldimethylsiloxy)benzaldehyde

Product 1

HCID 9888784HCID 9888784, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

100 mg (0.26 mmol) of 3,4-di(t-butyldimethylsiloxy)benzaldehyde was dissolved in 10 ml of THF under the atmosphere of argon at −40° C., and 0.30 ml of rare earth metal complex solution A1 was mixed into the solution. After stirring for 30 minutes, 79.3 mg (1.3 mmol) of nitromethane was added dropwise to the mixture. After 67-hour reaction time, 2 ml of 1 N aqueous solution of hydrochloric acid was added to stop the reaction. Then, after 50 ml of ethyl accetate was added, the mixture was subjected to oil-water separation twice with 20 ml of saturated salt solution and once with 20 ml of water, and the ethyl accetate layer was dehydrated with sodium sulfate anhydride and concentrated within evaporator, followed by the purification of the concentrate by silica gel chromatography (n-hexane/acetone=10/1), after which (R)-1-(3,4-di(t-butyldimethylsiloxy)phenyl)-2-nitroethanol with an optical purity of 92% e.e. was obtained in a yield of 93%.

Workup

  1. additionwas added
  2. customthe reaction
  3. additionThen, after 50 ml of ethyl accetate was added
  4. customthe mixture was subjected to oil-water separation twice with 20 ml of saturated salt solution and once with 20 ml of water
  5. concentrationconcentrated within evaporator
  6. customfollowed by the purification of the
  7. concentrationconcentrate by silica gel chromatography (n-hexane/acetone=10/1)

Sources & evidence

ORD record
ord-6022e130a1ab4e5099de857435bf0c9e
Source dataset
uspto-grants-2003_10
Patent number
US06632955B1

Reaction notes

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