Aluminium lithium hydride → 19-Trimethylsiloxy-5alpha-androstane-3beta,17beta-diol

HRID 1834969Notes

Reaction equation

HRID 1834969 reaction equation
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH2:23][O:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[O:29]C(=O)C)[CH2:6]1)(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH3:27][Si:25]([CH3:26])([CH3:28])[O:24][CH2:23][C@@:20]12[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C@@H:14]([OH:29])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C@H:7]1[CH2:6][C@@H:5]([OH:4])[CH2:22][CH2:21]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 8673543019-Trimethylsiloxy-5alpha-androstane-3beta,17beta-diol diacetate

Product 1

HCID 2280149619-Trimethylsiloxy-5alpha-androstane-3beta,17beta-diol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 19-trimethylsiloxy-5α-androstane-3β,17β-diol diacetate in ether is added to a lithium aluminum hydride suspension in ether. After refluxing for one hour, the excess hydride is destroyed with water. The ether solution is separated, dried over sodium sulfate and concentrated under vacuum. The residue which remains is crystallized from methanol to yield 19-trimethylsiloxy-5α-androstane-3β,17β-diol.

Workup

  1. temperatureAfter refluxing for one hour
  2. customthe excess hydride is destroyed with water
  3. customThe ether solution is separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue which remains is crystallized from methanol

Sources & evidence

ORD record
ord-85a9b9792fb045498aedef42c26b2c43
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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