Cyclohexanone, 4,4-dimethyl-2-(2-propenyl)- → HCID 54003456, compound

HRID 863179Notes

Reaction equation

HRID 863179 reaction equation
C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].[CH3:18][C:19]1([CH3:29])[CH2:24][CH2:23][C:22](=[O:25])[CH:21]([CH2:26][CH:27]=[CH2:28])[CH2:20]1>O1CCCC1.C(OCC)(=O)C>[CH3:18][C:19]1([CH3:29])[CH2:24][CH2:23][C@@H:22]([OH:25])[C@H:21]([CH2:26][CH:27]=[CH2:28])[CH2:20]1

Participants

5

Reactant 2

HCID 572869Cyclohexanone, 4,4-dimethyl-2-(2-propenyl)-HCID 16684435Lithium tritertbutoxyaluminohydride

Product 1

HCID 54003456HCID 54003456, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of lithium tri-tert-butoxyaluminohydride (460 mg) in dry tetrahydrofuran (3.5 ml) there was added a solution of 4,4-dimethyl-2-(2-propenyl)cyclohexanone (250 mg) at 0° C., and the mixture was stirred at room temperature for 2 hrs. The reaction was quenched by addition of water. The pH of the mixture was adjusted to pH 7 with 0.1N hydrochloric acid. The mixture was extracted with diethyl ether, and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. Purification of the residue by silica gel column chromatography (using n-hexane:ethyl acetate=20:1 as an eluent) gave (1R*,2R*)-4,4-dimethyl-2-(2-propenyl)cyclohexanol (185 mg, 73% yield) as a colorless oil; EI-MS: m/z 168 (M+); 1H-NMR (CDCl3)d: 0.90 (3H,s), 0.93 (3H,s), 1.2-1.8 (7H,m), 1.95 (1H,m), 2.46 (1H,m), 3.23 (1H,dt,J=5 & 11 Hz), 5.02 (1H,br.d,J=10 Hz), 5.06 (1H,br.d,J=17 Hz), 5.85 (1H,m).

Workup

  1. customThe reaction was quenched by addition of water
  2. extractionThe mixture was extracted with diethyl ether
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by silica gel column chromatography (

Sources & evidence

ORD record
ord-a6bb5ef18bbe4e65acdf316872459b7c
Source dataset
uspto-grants-1998_02
Patent number
US05719291

Reaction notes

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