Hydrochloric Acid → 21-Chloro-5alpha-pregnane-3,11,20-trione

HRID 1576801Notes

Reaction equation

HRID 1576801 reaction equation
O[CH2:2][C:3](=[O:25])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C:19](=[O:23])[CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([CH2:12][C:13](=[O:24])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.C1(C)C=CC(S([Cl:35])(=O)=O)=CC=1.Cl>N1C=CC=CC=1>[Cl:35][CH2:2][C:3](=[O:25])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C:19](=[O:23])[CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([CH2:12][C:13](=[O:24])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 7035523621-Hydroxy-5alpha-pregnane-3,11,20-trione

Product 1

HCID 8673403321-Chloro-5alpha-pregnane-3,11,20-trioneYield 35.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

21-Hydroxy-5α-pregnane-3,11,20-trione (3.0 g.) in anhydrous pyridine (15 ml.) was treated with toluene-4-sulphonyl chloride (3.0 g.) and the pale orange solution was stirred at room temperature for 3 hours. The cold solution was vigorously stirred during the slow addition of ice-cold water (200 ml.) and hydrochloric acid (2N;50 ml.). The yellow crystalline precipitate was filtered off, washed well with water and dried in vacuo at 60°, and the resulting crude product (2.4 g.) was recrystallized from acetone/petrol to give crude title compound (1.13 g.) as an off-white crystalline solid, m.p. 168°-172°, [α]D + 137° (c 1.13).

Workup

  1. filtrationThe yellow crystalline precipitate was filtered off
  2. washwashed well with water
  3. customdried in vacuo at 60°
  4. customthe resulting crude product (2.4 g.) was recrystallized from acetone/petrol

Sources & evidence

ORD record
ord-8449e9165542405d9f83fac9cc1e5797
Source dataset
uspto-grants-1976_09
Patent number
US03983111

Reaction notes

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