Trimethylsilylacetylene → 4-Ethynyl-4'-propylbicyclohexyl-4-ol

HRID 1532536

Reaction equation

HRID 1532536 reaction equation
C[Si]([C:5]#[CH:6])(C)C.[CH2:7]([CH:10]1[CH2:15][CH2:14][CH:13]([CH:16]2[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)[CH2:12][CH2:11]1)[CH2:8][CH3:9].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:5]([C:19]1([OH:22])[CH2:20][CH2:21][CH:16]([CH:13]2[CH2:12][CH2:11][CH:10]([CH2:7][CH2:8][CH3:9])[CH2:15][CH2:14]2)[CH2:17][CH2:18]1)#[CH:6]

Participants

5

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 4354185[1,1'-Bicyclohexyl]-4-one,4'-propyl-,HCID 11726816Tetrabutylammonium Fluoride Trihydrate

Product 1

HCID 183645044-Ethynyl-4'-propylbicyclohexyl-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

24.32 ml of (trimethylsilyl)acetylene are added dropwise at −30° C. to a solution of 30.0 g of 4′-propylbicyclohexyl-4-one and 3.41 g of tetrabutylammonium fluoride trihydrate in 300 ml of THF. The cooling bath is removed after 5 minutes, and the reaction mixture is stirred at RT for 2 hours. A suspension of 39.2 g of potassium fluoride in methanol is subsequently added, and the mixture is stirred at RT for 3 days. Conventional work-up gives 4-ethynyl-4′-propylbicyclohexyl-4-ol.

Workup

  1. customThe cooling bath is removed after 5 minutes
  2. additionA suspension of 39.2 g of potassium fluoride in methanol
  3. additionis subsequently added
  4. stirringthe mixture is stirred at RT for 3 days

Sources & evidence

ORD record
ord-7318a6bb722d4e8aa364de8945e408bd
Source dataset
uspto-grants-2001_03
Patent number
US06203724B1

Linked notes

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