Tetrahydrofuran → (7-alpha,17 beta)-17-(Acetyloxy)-7-propylestr-4-en-3-one

HRID 428302Notes

Reaction equation

HRID 428302 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C@@H:19]1[C:14](=[CH:15][C:16](=[O:23])[CH2:17][CH2:18]1)[CH:13]=[CH:12]3)(=[O:3])[CH3:2].[NH4+].[Cl-].[CH2:26]1[CH2:30]OC[CH2:27]1>>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:6]12[CH3:7])[C@@H:19]1[C:14](=[CH:15][C:16](=[O:23])[CH2:17][CH2:18]1)[CH2:13][C@H:12]3[CH2:27][CH2:26][CH3:30])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 11088332(17beta)-3-Oxoestra-4,6-dien-17-yl acetate

Product 1

HCID 15380111(7-alpha,17 beta)-17-(Acetyloxy)-7-propylestr-4-en-3-one

Procedure

After stirring for an additional 0.5 hr , a solution of 5.2 g of (17 beta)-17-(acetyloxy)estra-4,6-dien-3-one (1) in 20 ml of THF was added dropwise at −40 C. Upon stirring for an additional 15 minutes the reaction was complete, and the mixture was poured onto 300 ml of saturated NH4Cl solution, followed by extraction with ethyl acetate. The organic material, isolated after washing, drying and evaporation of the solvent, was taken up in 30 ml of THF and stirred in the presence of 3 ml of 6N H2SO4 to isomerize some Δ5,6 isomer to Δ4,5 isomer. After 1 hr the mixture was neutralized with saturated NaHCO3 solution and extracted with ethyl acetate. Chromatography of the crude product over silica gel (heptane/ethyl acetate 8/2) provided 2.1 g of 2, m.p. 97-100° C.

Workup

  1. stirringUpon stirring for an additional 15 minutes the reaction
  2. extractionfollowed by extraction with ethyl acetate
  3. customThe organic material, isolated
  4. washafter washing
  5. customdrying
  6. customevaporation of the solvent
  7. stirringstirred in the presence of 3 ml of 6N H2SO4
  8. waitAfter 1 hr the mixture was neutralized with saturated NaHCO3 solution
  9. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-84d52c6b99e742608132d37701c5abc1
Source dataset
uspto-grants-2001_11
Patent number
US06313180B1

Reaction notes

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