Hydrochloric Acid → HCID 9888784, compound

HRID 1271621Notes

Reaction equation

HRID 1271621 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 with an 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 with an evaporator
  6. customfollowed by the purification of the
  7. concentrationconcentrate by silica gel chromatography (n-hexane/acetone=10/1)

Sources & evidence

ORD record
ord-b8b411c8f99149d5a0be89f545abfaf3
Source dataset
uspto-grants-2007_04
Patent number
US07205425B2

Reaction notes

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