Water → HCID 22797468, compound

HRID 371823Notes

Reaction equation

HRID 371823 reaction equation
C([O:4][CH2:5][C@@:6]12[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C@@H:18]([O:24][Si:25]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]1=[CH:10][C@@H:9]([O:44][Si:45]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH2:8][CH2:7]2)(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>CCOCC>[C:58]1([Si:45]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[O:44][C@H:9]2[CH2:8][CH2:7][C@@:6]3([CH2:5][OH:4])[C:11]([CH2:12][CH2:13][C@@H:14]4[C@@H:23]3[CH2:22][CH2:21][C@@:19]3([CH3:20])[C@H:15]4[CH2:16][CH2:17][C@@H:18]3[O:24][Si:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)=[CH:10]2)[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22797467HCID 22797467, compound

Product 1

HCID 22797468HCID 22797468, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To an ether solution of 3β,17β-di-(triphenylsiloxy)androst-4-en-19-ol acetate is added a suspension of lithium aluminum hydride in ether. After refluxing for a period of one hour, water is cautiously added, the ether solution is separated, dried over sodium sulfate and evaporated under reduced pressure. The residue when purified from an acetone-hexane mixture results in the preparation of the desired 3β,17β-di-(triphenylsiloxy)androst-4-en-19-ol.

Workup

  1. temperatureAfter refluxing for a period of one hour
  2. customthe ether solution is separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue when purified from an acetone-hexane mixture

Sources & evidence

ORD record
ord-2a43f829e2a94cc1bae59cf68e556b6d
Source dataset
uspto-grants-1978_05
Patent number
US04087524

Reaction notes

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