Isopropanol → HCID 70505970, compound

HRID 2418147Notes

Reaction equation

HRID 2418147 reaction equation
[C:1]([O:9][C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@@:12]3([O:40][C@@H:13]3[C@@H:14](Cl)[C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[C@@H:17]3[CH2:38][C@@H:18]3[C@@H:19]2[O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(O)C.CC(C)=O.C(OC(C)C)(C)C>C(O)(=O)C.[Zn]>[C:1]([O:9][C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@:12]([OH:40])([CH:13]=[CH:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[C@@H:17]3[CH2:38][C@@H:18]3[C@@H:19]2[O:29][C:30](=[O:37])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 22221350Acetone diisopropyl etherHCID 88717966HCID 88717966, compound

Product 1

HCID 70505970HCID 70505970, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Analogously to Example 2, 13.5 g of 3β,17β-dibenzoyloxy-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstane is reacted in 130 ml of acetic acid and 130 ml of propan-2-ol with 49.5 g of zinc dust and worked up. Chromatography on silica gel yields 8.8 g of 3β,17β-dibenzoyloxy-15β,16β-methylene-5β-androst-6-en-5-ol, mp 223°-225° C. (acetone-diisopropyl ether).

Sources & evidence

ORD record
ord-54c4495ebbf44f6e95b35d50daecb4fa
Source dataset
uspto-grants-1984_09
Patent number
US04472310

Reaction notes

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