Triethylamine → HCID 178477217, compound

HRID 1456349Notes

Reaction equation

HRID 1456349 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([CH:16]([OH:18])[CH3:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Si:26](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27].C(OCC)(=O)C>CS(C)=O>[CH2:1]([O:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([CH:16]([O:18][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH3:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 178468166HCID 178468166, compound

Product 1

HCID 178477217HCID 178477217, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 50 ml of dry dimethyl sulfoxide were dissolved 2.0 g of trans-4-benzyloxymethyl-1-(1-hydroxyethyl)cyclohexane, and 2.24 ml of triethylamine and 1.88 g of t-butyldimethylsilyl chloride were added thereto with stirring at room temperature, and the mixture was stirred at room temperature for 2 hours and 50 minutes. To the reaction mixture were added 200 ml of ethyl acetate, and the mixture was washed successively with an aqueous citric acid solution, an aqueous sodium chloride solution, an aqueous sodium bicarbonate solution and an aqueous sodium chloride solution. The mixture was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: cyclohexane/ethyl acetate=50/1) to obtain 2.76 g of the desired compound as a colorless oil.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at room temperature for 2 hours and 50 minutes
  3. washthe mixture was washed successively with an aqueous citric acid solution
  4. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: cyclohexane/ethyl acetate=50/1)

Sources & evidence

ORD record
ord-beb306d2a0f4419ba698be24925d396c
Source dataset
uspto-grants-1998_12
Patent number
US05843973

Reaction notes

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