Hydrochloric Acid → HCID 86733309, compound

HRID 1606377Notes

Reaction equation

HRID 1606377 reaction equation
[OH:1][C@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH:10]=[C:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.Cl>N1C=CC=CC=1>[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30]([O:1][C@H:2]2[CH2:21][CH2:20][C@@:19]3([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]4[C@@H:18]3[CH2:17][CH2:16][C@@:15]3([CH3:23])[C@H:8]4[CH2:9][CH:10]=[C:11]3[C:12](=[O:14])[CH3:13])[CH2:3]2)(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 1775252(3β,5α)-3-Hydroxypregn-16-en-20-one

Product 1

HCID 86733309HCID 86733309, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3β-Hydroxy-5α-pregn-16-en-20-one (10 g.) in pyridine (50 ml.) was treated with toluene-p-sulphonyl chloride (10 g.), and the solution was stirred at room temperature overnight and then poured into dilute hydrochloric acid. The precipitate was extracted into chloroform, and the extract was washed with dilute hydrochloric acid and with water, dried over sodium sulphate and evaporated to an oil which crystallised on standing. Recrystallisation from ethyl acetate/petrol gave 3β-toluene-p-sulphonyloxy-5α-pregn-16-en-20-one (13.3g) as off-white prisms, m.p. 146°-148° , [α]D + 24.0°, λmax. (EtOH) 226.5 nm (ε 18,600), 240 nm (infl.) (ε 9550), 272.5 nm (ε 518).

Workup

  1. extractionThe precipitate was extracted into chloroform
  2. washthe extract was washed with dilute hydrochloric acid and with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated to an oil which
  5. customcrystallised
  6. customRecrystallisation from ethyl acetate/petrol

Sources & evidence

ORD record
ord-f6c26d8628ad4f6eb18ed8a7cce8189e
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

Loading…