Water → HCID 69873851, compound

HRID 479316Notes

Reaction equation

HRID 479316 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:15][C@H:16]1[CH2:40][CH2:39][C@@:38]2([CH3:41])[C:18](=[CH:19][CH2:20][C@@H:21]3[C@@H:37]2[CH2:36][CH2:35][C@@:34]2([CH3:42])[C@H:22]3[CH2:23][C@H:24]([O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45])[C@@H:25]2[C@H:26]([CH3:33])[CH2:27][CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:17]1)(=O)C1C=CC=CC=1.O>C(OCC)C>[Si:44]([O:43][C@H:24]1[CH2:23][C@@H:22]2[C@:34]([CH3:42])([CH2:35][CH2:36][C@H:37]3[C@H:21]2[CH2:20][CH:19]=[C:18]2[C@:38]3([CH3:41])[CH2:39][CH2:40][C@H:16]([OH:15])[CH2:17]2)[C@H:25]1[C@H:26]([CH3:33])[CH2:27][CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])([C:47]([CH3:48])([CH3:49])[CH3:50])([CH3:45])[CH3:46]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 67551563HCID 67551563, compound

Product 1

HCID 69873851HCID 69873851, compoundYield 108%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
40 °C

Procedure

To a suspension of lithium aluminium hydride (4.5 g, 120 mmol) in diethyl ether (700 mL) was added, dropwise 16β-(tert-butyldimethylsilyloxy)cholest-5-en-3β-yl benzoate (8.1 g, 12 mmol) in diethyl ether (50 mL). After stirring at room temperature for 15 minutes and at 40° C. for 0.5 hour, water was added. The inorganic impurities were removed by filtration through Celite, and after removal of solvent under reduced pressure the residue was purified by flash chromatography to give 16β-(tert-butyldimethylsilyloxy)cholest-5-en-3β-ol (6.7 g).

Workup

  1. additionwas added
  2. customThe inorganic impurities were removed by filtration through Celite
  3. customafter removal of solvent under reduced pressure the residue
  4. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-3c94364422b34b7092556ef06bcc0d66
Source dataset
uspto-grants-2003_11
Patent number
US06645953B2

Reaction notes

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