HCID 18652184, compound → HCID 18652188, compound

HRID 1587029Notes

Reaction equation

HRID 1587029 reaction equation
C(OC[O:10][C@@H:11]1[C@@:27]2([CH3:28])[C@@H:23]([CH2:24][CH2:25][C@@H:26]2[CH:29]([CH3:45])[CH2:30][CH:31]=[C:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C@H:22]2[C@@H:13]([C@:14]3([CH3:62])[C@H:19]([CH2:20][C@H:21]2[O:46][Si](C(C)(C)C)(C)C)[CH2:18][C@H:17]([O:54][Si](C(C)(C)C)(C)C)[CH2:16][CH2:15]3)[CH2:12]1)C1C=CC=CC=1>CCOCC.C(S)C.[Cl-].[Zn+2].[Cl-]>[OH:54][C@@H:17]1[CH2:16][CH2:15][C@@:14]2([CH3:62])[C@H:19]([CH2:20][C@@H:21]([OH:46])[C@@H:22]3[C@@H:13]2[CH2:12][C@H:11]([OH:10])[C@@:27]2([CH3:28])[C@H:23]3[CH2:24][CH2:25][C@@H:26]2[CH:29]([CH3:45])[CH2:30][CH:31]=[C:32]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:18]1

Participants

5

Reactant 1

HCID 18652184HCID 18652184, compound

Product 1

HCID 18652188HCID 18652188, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent2×HCID 6343EthanethiolSolvent

Procedure

A mixture of 12α-benzyloxymethoxy-3α,7α-di-tert-butyldimethylsilyloxy-17β-[(1,1-diphenyl)-1-penten-4-yl]-5β-androstane (4.63 g), 1M zinc chloride in ether (10.5 ml) and ethanethiol (2.0 ml) in ether (10 ml) is stirred at room temperature for about 30 minutes. The mixture is concentrated in vacuo and the residue taken up in ether. The ether solution is washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo to give the desired product.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. washThe ether solution is washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d3e6cd1a515480693d360583d1c8537
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

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