Ethyl (3,3,5,5-tetramethylcyclohexylidene)acetate → HCID 22630144, compound

HRID 2307076Notes

Reaction equation

HRID 2307076 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1([CH3:22])[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][C:10](=[CH:16][C:17](OCC)=[O:18])[CH2:9]1>CCOCC>[CH3:7][C:8]1([CH3:22])[CH2:13][C:12]([CH3:14])([CH3:15])[CH2:11][C:10](=[CH:16][CH2:17][OH:18])[CH2:9]1

Participants

4

Reactant 2

HCID 15307456Ethyl (3,3,5,5-tetramethylcyclohexylidene)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 22630144HCID 22630144, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of LiAlH4 (1.7 g, 45 mmol) in dry ether (60 ml) a solution of acetate 2 (3.2 g, 15 mmol) in ether (20 ml) was added dropwise while cooling with ice water. Stirring was continued for 1 h and the residual LiAlH4 was destroyed with water. The aqueous layer was separated and twice extracted with ether (30 ml). The combined extracts were washed with brine (50 ml) and dried over MgSO4. After concentration in vacuo an oily residue was purified by Kugelrohr short path distillation (150-170° C., 11 mm Hg) to give 3 (2.3 g, 89%) as an oil. 1H NMR (CDCl3, TMS): 0.92 (6H, s, 3,5-CH3); 1.10 (1H, br s, OH); 1.28 (2H, s, 4-CH2); 1.87 and 1.94 (total 4H, both s, 2,6-CH2); 4.16 (2H, d, 7 Hz, CH2O) and 5.50 ppm (1H, t, 7 Hz, ═C—H).

Workup

  1. customthe residual LiAlH4 was destroyed with water
  2. customThe aqueous layer was separated
  3. extractiontwice extracted with ether (30 ml)
  4. washThe combined extracts were washed with brine (50 ml)
  5. dry with materialdried over MgSO4
  6. concentrationAfter concentration in vacuo an oily residue
  7. distillationwas purified by Kugelrohr short path distillation (150-170° C., 11 mm Hg)

Sources & evidence

ORD record
ord-dd1d564dee134db49a3d23e7e0df410c
Source dataset
uspto-grants-2004_12
Patent number
US06828462B2

Reaction notes

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