2-Chloroethanol → HCID 22789153, compound

HRID 1606354Notes

Reaction equation

HRID 1606354 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.C(=O)(O)[O-].[Na+].O.[Cl:31][CH2:32][CH2:33][OH:34]>S(=O)(=O)(O)O>[Cl:31][CH2:32][CH2:33][O:34][C@H:2]1[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][C@@H:3]1[OH:1]

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 962WaterHCID 516892Sodium BicarbonateHCID 86733130HCID 86733130, compound

Product 1

HCID 22789153HCID 22789153, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

2α,3α-Epoxy-5α-pregnane-11,20-dione (1 g.) was dissolved in 2-chloroethanol (50 ml.) and concentrated sulphuric acid (6 drops) added to the solution. The mixture was stirred at room temperature for 1 hour, neutralised with sodium bicarbonate solution and poured into water (500 ml.). The precipitate formed was extracted into ether (2 × 100 ml.) and the combined extracts washed with water (2 × 100 ml.). The organic layer was dried over anhydrous sodium sulphate and evaporated to a yellow oil (1.5 g.) which was purified by preparative tlc using ethyl acetatepetroleum ether, 1/1 run 3 times. The main band (RF ~0.2 - 0.3) gave the title compound (640 mg.) as an off-white foam identical with a previously prepared sample.

Workup

  1. customThe precipitate formed
  2. extractionwas extracted into ether (2 × 100 ml.)
  3. washthe combined extracts washed with water (2 × 100 ml.)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. customevaporated to a yellow oil (1.5 g.) which
  6. customwas purified by preparative tlc

Sources & evidence

ORD record
ord-a57bcac258234f1188ce7987898ee59a
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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