Sodium Hydroxide → HCID 14702282, compound

HRID 894504Notes

Reaction equation

HRID 894504 reaction equation
FC(F)(F)C([O:5][CH:6]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C:8](=[CH:9][CH2:10][C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C:12]3=[CH:13][CH2:14][C:15]2=[O:25])[CH2:7]1)=O.[OH-].[Na+]>O1CCCC1.CO.O>[OH:5][C@H:6]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C:8](=[CH:9][CH2:10][C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C:12]3=[CH:13][CH2:14][C:15]2=[O:25])[CH2:7]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 53886518HCID 53886518, compound

Product 1

HCID 14702282HCID 14702282, compoundYield 97.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Trifluoroacetoxyandrost-5(6),14-dien-17-one (15 mg) in tetrahydrofuran (3 ml) and methanol (2 ml) was treated with 2 N aqueous sodium hydroxide (1 ml) at 0° for 3 min. The solution was diluted with water (15 ml), the organic solvents were evaporated off in vacuo, and the residue was extracted with ether to give the title compound (11 mg), which crystallized from acetone-hexane as prisms (8 mg), m.p. 161°-164°, identical [IR and t.l.c. (ethyl acetate-hexane 1:3)] with an authentic sample. Two recrystallizations raised the m.p. to 165°-168°.

Workup

  1. customthe organic solvents were evaporated off in vacuo
  2. extractionthe residue was extracted with ether

Sources & evidence

ORD record
ord-a4aa65ad61ca453c8a8cecd46f1129f4
Source dataset
uspto-grants-1981_08
Patent number
US04284558

Reaction notes

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