Hydrochloric Acid → HCID 67652594, compound

HRID 2393216Notes

Reaction equation

HRID 2393216 reaction equation
Br[C@@H:2]1[CH2:7][C@H:6]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:4]2([CH3:5])[C:3]1=[O:22])[C@:16]1([CH3:17])[C:11]([CH2:12][C@@H:13]([CH3:21])[CH2:14][CH2:15]1)=[CH:10][CH2:9]3.[OH-:23].[Na+].Cl.[CH3:26]N(C)C=O>O>[OH:23][C@@H:2]1[CH2:7][C@H:6]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:4]2([CH3:5])[C:3]1=[O:22])[C@:16]1([CH3:17])[C:11]([CH2:12][C@@H:13]([CH2:21][CH3:26])[CH2:14][CH2:15]1)=[CH:10][CH2:9]3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 56624888HCID 56624888, compound

Product 1

HCID 67652594HCID 67652594, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

16α-Bromo-3β-methylandrost-5-en-17-one (1.00 g, 2.74 mmol) was dissolved in dimethylformamide (90 mL). Sodium hydroxide (165 mg, 4.1 mmol) in water (10 mL) was added and the solution stirred for 2 h. at room temperature. The solution was poured into 1% HCl (200 mL) and extracted with ethyl acetate (2×50 mL). The organic layer was washed with 5% sodium biocarbonate, water, then dried over magnesium sulfate and filtered. Evaporation gave a pale yellow solid which was chromatographed on flash silica gel and eluted with ether/hexane (10/90). Recrystallization from ether gave 0.54 g (65%) 16α-hydroxy-3β-ethylandrost-5-en-17-one mp 166°-168° C.; NMR (DMSO-d6) δ5.30 (br s, 1H, H-3), 4.38 (t, 1H, 16β-H), 2.0-1.05 (m, complex), 0.98 (s, 3H, C-19 Me), 0.95 (d, J=8 Hz, 3H, C-3 Me), 0.87 Cs, 3H, C-18 Me); IR (KBr) 3440, 2900, 1735, 1445, 1365, 1010; MS 302 (M+, 100), 287(24), 274(7), 259(7), 241(7), 230(72), 215(41), 159(31); Anal. Calcd for C20 H30O2 : C, 79.42; H, 9.99. Found: C, 79.24; H, 10.04.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe organic layer was washed with 5% sodium biocarbonate, water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customEvaporation
  6. customgave a pale yellow solid which
  7. customwas chromatographed on flash silica gel
  8. washeluted with ether/hexane (10/90)
  9. customRecrystallization from ether

Sources & evidence

ORD record
ord-15b82e2355e14e5c84c2fc76c5db4ff9
Source dataset
uspto-grants-1998_09
Patent number
US05804576

Reaction notes

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