Isopropanol → HCID 70507076, compound

HRID 2418142Notes

Reaction equation

HRID 2418142 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]2[CH2:11][C@H:9]2[C@H:8]2[C@H:12]3[C@H:22]([CH2:23][CH2:24][C@:6]12[CH3:7])[C@:20]1([CH3:21])[C@@:15]2([O:34][C@@H:14]2[C@H:13]3Cl)[CH2:16][C@@H:17]([O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:18][CH2:19]1)(=[O:3])[CH3:2].CC(O)C>C(O)(=O)C.[Zn]>[C:1]([O:4][C@H:5]1[C@H:10]2[CH2:11][C@H:9]2[C@H:8]2[C@H:12]3[C@H:22]([CH2:23][CH2:24][C@:6]12[CH3:7])[C@:20]1([CH3:21])[C@@:15]([OH:34])([CH2:16][C@@H:17]([O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:18][CH2:19]1)[CH:14]=[CH:13]3)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 88717469HCID 88717469, compound

Product 1

HCID 70507076HCID 70507076, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

200 mg of 17β-acetoxy-3β-benzoyloxy-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstane is stirred in 4 ml of acetic acid and 4 ml of propan-2-ol with 800 mg of zinc dust for 1 hour at 80° C. The mixture is filtered off from the zinc, washed with diethyl ether, and worked up analogously to Example 1. After chromatography and recrystallization from diisopropyl ether-acetone, 135 mg of 17β-acetoxy-3β-benzoyloxy-15β,16β-methylene-5β-androst-6-en-5-ol is obtained, mp 212°-212.5° C.

Workup

  1. filtrationThe mixture is filtered off from the zinc
  2. washwashed with diethyl ether
  3. customAfter chromatography and recrystallization from diisopropyl ether-acetone

Sources & evidence

ORD record
ord-c2fbf1e1d3e34f6c993686c285a81754
Source dataset
uspto-grants-1984_09
Patent number
US04472310

Reaction notes

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