Triethylamine → HCID 178455226, compound

HRID 1456354Notes

Reaction equation

HRID 1456354 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][OH:10])[CH2:5][CH2:4]1.C(N(CC)CC)C.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].C(OCC)(=O)C>CN(C)C=O>[Si:18]([O:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][OH:10])[CH2:5][CH2:4]1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 178520956HCID 178520956, compound

Product 1

HCID 178455226HCID 178455226, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In 250 ml of dry dimethylformamide were dissolved 10.0 g of trans-1,4-dihydroxymethylcyclohexane and 14.5 ml of triethylamine, and a solution of 10.24 g of t-butyldimethylsilyl chloride dissolved in 50 ml of dry dimethylformamide was added dropwise thereto with stirring under ice-cooling, and the resulting mixture was stirred under ice-cooling for 1 hour. To the reaction mixture were added 200 ml of ethyl acetate, the precipitated triethylamine hydrochloride was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography employing cyclohexane-ethyl acetate (2:1) as an eluting solvent to obtain 11.9 g of the desired compound as a colorless oil.

Workup

  1. additionwas added dropwise
  2. temperaturecooling
  3. stirringthe resulting mixture was stirred under ice-
  4. temperaturecooling for 1 hour
  5. customthe precipitated triethylamine hydrochloride was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ac76bbac7e82458faee7b5b99fb411f9
Source dataset
uspto-grants-1998_12
Patent number
US05843973

Reaction notes

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