Methanol → HCID 86733129, compound

HRID 267612Notes

Reaction equation

HRID 267612 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:20]([CH3:22])([CH2:21][C@@H:2]12)[C@@H:19]1[C@H:8]([C@H:9]2[C@:16]([CH3:24])([CH2:17][C:18]1=[O:23])[C@@H:12]([C:13](=[O:15])[CH3:14])[CH2:11][CH2:10]2)[CH2:7][CH2:6]3.S(=O)(=O)(O)O.[OH2:30].[CH3:31]O>>[OH:30][C@@H:3]1[C@@H:2]([O:1][CH3:31])[CH2:21][C@@:20]2([CH3:22])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:19]2[C:18](=[O:23])[CH2:17][C@@:16]2([CH3:24])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:13](=[O:15])[CH3:14])[CH2:4]1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 86733130HCID 86733130, compound

Product 1

HCID 86733129HCID 86733129, compound

Procedure

2α,3α-Epoxy-5α-pregnane-11,20-dione (200 mg) was dissolved in dry methanol (20 ml), and concentrated sulphuric acid (0.1 ml.) was added. The solution was stirred at room temperature for 20 minutes, and then poured into water (125 ml.) to give a white crystalline precipitate which was filtered off and dried in vacuo over phosphorus pentoxide to give 3α-hydroxy-2β-methoxy-5α-pregnane-11,20-dione (175 mg.), m.p. 163°-164°, [α]D + 109°.

Workup

  1. customto give a white crystalline precipitate which
  2. filtrationwas filtered off
  3. dry with materialdried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-5ab51b16e0c141ad8f2feb20f629f41b
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

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