4-tert-Butylcyclohexanone → HCID 10911276, compound

HRID 2407605Notes

Reaction equation

HRID 2407605 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH2:12]([Si:15](C)([CH3:17])[CH3:16])C=C.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[C:1]([CH:5]1[CH2:6][CH2:7][C:8]([O:11][Si:15]([CH3:17])([CH3:16])[CH3:12])=[CH:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 73924-tert-ButylcyclohexanoneHCID 8471TriethylamineHCID 69808AllyltrimethylsilaneHCID 516892Sodium Bicarbonate

Product 1

HCID 10911276HCID 10911276, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Into a two-necked flask were placed 4-tert-butylcyclohexanone (74.1 mg, 0.480 mmol), and toluene (5.0 ml) as a solvent, and the mixture was subjected to heating under reflux conditions under an argon atmosphere. After the start of the refluxing, allyltrimethylsilane (82.3 mg, 0.720 mmol) was added, and a solution (0.1 M) of triflic imide (1.35 mg, 4.80 μmol) in toluene was added dropwise. After 5 min, triethylamine (0.486 mg, 4.80 μmol) was added, and the mixture was reacted for 10 min. Thereafter, cooled aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with hexane and dried over sodium sulfate. The solvent was evaporated under reduced pressure and purified by column chromatography to give the object product 4-tert-butyl-1-trimethylsilyloxy-1-cyclohexene (yield 88%).

Workup

  1. customInto a two-necked flask were placed
  2. temperatureto heating under reflux conditions under an argon atmosphere
  3. customthe mixture was reacted for 10 min
  4. additionwas added
  5. extractionthe mixture was extracted with hexane
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-2daad67c6fdd4e6fb4e6e52045222baa
Source dataset
uspto-grants-2014_08
Patent number
US08809567B2

Reaction notes

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