Sodium Bicarbonate → HCID 11780000, compound

HRID 574264Notes

Reaction equation

HRID 574264 reaction equation
[C:1]([Si:5]([CH3:24])([CH3:23])[O:6][C@H:7]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:8][O:9][Si](C(C)(C)C)(C)C)([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+]>CO>[C:1]([Si:5]([CH3:24])([CH3:23])[O:6][CH:7]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:8][OH:9])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67144432HCID 67144432, compound

Product 1

HCID 11780000HCID 11780000, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [(R)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-benzene (625 mg, 1.7 mmol) in methanol (3 mL) was slowly added ferric chloride III) (276 mg, 1.7 mmol) with stirring at room temperature. When the reaction was monitored to be completed about 25 min after the addition, an aqueous saturated sodium bicarbonate solution was added. The solution was extracted with ethyl ether and the organic layer thus formed was separated. To the organic layer was added sodium sulfate, followed by stirring for 5 min and filtering. The filtrate was concentrated and dried in a vacuum, and the residue was purified using silica gel chromatography (eluent: hexane/ethyl acetate, 16/1) and dried in a vacuum to afford 270 mg of the compound as a colorless oil (yield 63%).

Workup

  1. additionafter the addition
  2. extractionThe solution was extracted with ethyl ether
  3. customthe organic layer thus formed
  4. customwas separated
  5. additionTo the organic layer was added sodium sulfate
  6. stirringby stirring for 5 min
  7. filtrationfiltering
  8. concentrationThe filtrate was concentrated
  9. customdried in a vacuum
  10. customthe residue was purified
  11. customdried in a vacuum

Sources & evidence

ORD record
ord-e46c22891c644344a5fad821716819f3
Source dataset
uspto-grants-2015_05
Patent number
US09034850B2

Reaction notes

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