Water → HCID 20599272, compound

HRID 479320Notes

Reaction equation

HRID 479320 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:36])[C:32](=[O:33])[CH2:31][CH2:30][C@@:29]2([CH3:34])[C:9]1=[CH:10][CH2:11][C@@H:12]1[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:35])[C@H:13]1[CH2:14][CH:15]=[C:16]2[C@H:17]([CH3:24])[CH2:18][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22].O>C(OCC)C>[OH:33][C@H:32]1[CH2:31][CH2:30][C@@:29]2([CH3:34])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:35])[C@H:13]3[CH2:14][CH:15]=[C:16]2[C@H:17]([CH3:24])[CH2:18][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:8]1([CH3:36])[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 67551506HCID 67551506, compound

Product 1

HCID 20599272HCID 20599272, compoundYield 106.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminium hydride (80 mg, 2 mmol) in diethyl ether (15 mL) was added 4,4-dimethylcholesta-5,16-dien-3-one (220 mg, 0.5 mmol) in 10 mL ether and the whole was stirred for 1.5 hours. Water was added and the solution filtered through a plug of Celite. The aqueous phase was extracted with ether, washed with 4N HCl, brine, dried over magnesium sulphate and concentrated under reduced pressure to give 3β-hydroxy-4,4-dimethylcholesta-5,16-diene (220 mg).

Workup

  1. filtrationthe solution filtered through a plug of Celite
  2. extractionThe aqueous phase was extracted with ether
  3. washwashed with 4N HCl, brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-099db5c7862a48b5a30e3fc3dcf4209b
Source dataset
uspto-grants-2003_11
Patent number
US06645953B2

Reaction notes

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