Water → HCID 86736330, compound

HRID 1390788Notes

Reaction equation

HRID 1390788 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:25]([CH2:26][CH2:27][C@:6]12[CH3:7])[C@:19]1([CH2:20][O:21][C:22](=[O:24])[CH3:23])[C:14]([CH2:15][C@@H:16]([OH:28])[CH2:17][CH2:18]1)=[CH:13][CH2:12]3)(=[O:3])[CH3:2].F[B-](F)(F)F.[CH2:34]([O+](CC)CC)[CH3:35].O>C(Cl)Cl>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:25]([CH2:26][CH2:27][C@:6]12[CH3:7])[C@:19]1([CH2:20][O:21][C:22](=[O:24])[CH3:23])[C:14]([CH2:15][C@@H:16]([O:28][CH2:34][CH3:35])[CH2:17][CH2:18]1)=[CH:13][CH2:12]3)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 2723982Triethyloxonium tetrafluoroborateHCID 70604761HCID 70604761, compound

Product 1

HCID 86736330HCID 86736330, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Androstene-3β,17β,19-triol 17,19-diacetate is dissolved in methylenechloride and triethyloxonium fluoroborate added thereto. After stirring for a period of about two hours at room temperature, water is added to the reaction mixture. The methylenechloride layer is dried over magnesium sulfate and concentrated to dryness. The residue is crystallized from an acetone-hexane mixture to yield the desired 3β-ethoxy-5-androstene-17β,19-diol diacetate.

Workup

  1. dry with materialThe methylenechloride layer is dried over magnesium sulfate
  2. concentrationconcentrated to dryness
  3. customThe residue is crystallized from an acetone-hexane mixture

Sources & evidence

ORD record
ord-65f4e78653ba4f05b345502968f47227
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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