Tetrahydrofuran → HCID 56625789, compound

HRID 2418148Notes

Reaction equation

HRID 2418148 reaction equation
[OH:1][C@H:2]1[CH2:20][CH2:19][C@@:18]2([CH3:21])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:17]2[CH2:16][CH2:15][C@@:12]2(C=O)[C@H:8]3[C@@H]3C[C@@H]3[CH2:11]2)[CH2:3]1.C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].[O:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1>C(OCC)C>[CH2:41]1[C@@H:43]2[C@H:44]([OH:40])[C@:12]3([CH2:15][CH2:16][C@H:17]4[C@@H:7]([CH2:6][CH:5]=[C:4]5[C@:18]4([CH3:21])[CH2:19][CH2:20][C@H:2]([OH:1])[CH2:3]5)[C@@H:8]3[C@H:42]12)[CH3:11]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 16684435Lithium tritertbutoxyaluminohydrideHCID 88717387HCID 88717387, compound

Product 1

HCID 56625789HCID 56625789, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 21 g of 3β-hydroxy-15β,16β-methylene-5-androsten-18-one in 210 ml of tetrahydrofuran was stirred with 21 g of lithium tri-tert.-butoxyaluminohydride for 1 hour at room temperature. The mixture was then diluted with diethyl ether, washed with 2N sulfuric acid and water, dired, and evaporated, thus obtaining 19 g of 15β,16β-methylene-5-androstene-3β,17β-diol, used without further purification in the subsequent stage.

Workup

  1. washwashed with 2N sulfuric acid and water
  2. customdired, and evaporated

Sources & evidence

ORD record
ord-1ac249e6e4324c51b00e8905e58f657c
Source dataset
uspto-grants-1984_09
Patent number
US04472310

Reaction notes

Loading…