Water → HCID 86738408, compound

HRID 1156047Notes

Reaction equation

HRID 1156047 reaction equation
[CH2:1]([C@H:3]1[CH2:9][C@H:8]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:5]2([CH2:6][CH3:7])[C:4]1=[O:24])[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[CH:14][C:13]=1[CH2:12][CH2:11]3)[CH3:2].O>C(O)(=O)C.Cl>[CH2:1]([C@@H:3]1[CH2:9][C@H:8]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:5]2([CH2:6][CH3:7])[C@H:4]1[OH:24])[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[CH:14][C:13]=1[CH2:12][CH2:11]3)[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 86738407HCID 86738407, compound

Product 1

HCID 86738408HCID 86738408, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1.3 g of 16β-ethyl-3-methoxy-18-methyl-1,3,5(10)-estratrien-17-one in 14.5 ml of glacial acetic acid and 2 ml of concentrated hydrochloric acid is stirred for 16 hours at room temperature. Then the mixture is poured into water, extracted with ethyl acetate, the ethyl acetate extracts washed in succession with saturated NaHCO3 solution and saturated NaCl solution, dried over sodium sulfate, and concentrated under vacuum. The oily crude product is reduced according to 1(d) with sodium borohydride. Chromatography on silica gel with petroleum ether/ethyl acetate yields 620 mg of 16α-ethyl-3-methoxy-18-methyl-1,3,5(10)-estratrien-17β-ol, m.p. 112°-114° C. (from methanol).

Workup

  1. extractionextracted with ethyl acetate
  2. washthe ethyl acetate extracts washed in succession with saturated NaHCO3 solution and saturated NaCl solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-fc9d0c5a8e7f4bcd9adb0ae2125652b7
Source dataset
uspto-grants-1982_06
Patent number
US04333928

Reaction notes

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