Sodium Hydroxide → HCID 14702282, compound

HRID 259221Notes

Reaction equation

HRID 259221 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 2N 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-41542a3b605944e699e3e65b8f2ddd7c
Source dataset
uspto-grants-1977_07
Patent number
US04036864

Reaction notes

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