Tetrahydrofuran → HCID 12135229, compound

HRID 1369371Notes

Reaction equation

HRID 1369371 reaction equation
[CH3:1][C:2](C)([O-])[CH3:3].[K+].C[C@@H]1C[C:24]2[CH2:23][C:22](=[O:26])[CH2:21][CH2:20][C:19]=2[C@@H:18]2[C@@H:9]1[C@H:10]1[C@@:14]([CH2:16][CH2:17]2)([CH3:15])[C@@H:13](O)[CH2:12][CH2:11]1.[CH2:28]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:28][C@@H:17]1[CH2:16][C:14]2[CH2:15][C:2](=[CH2:1])[CH2:3][CH2:9][C:10]=2[C@@H:11]2[C@@H:18]1[C@H:19]1[C@@:20]([CH2:13][CH2:12]2)([CH3:21])[C@@H:22]([OH:26])[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 12135243HCID 12135243, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 12135229HCID 12135229, compound

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

Methyltriphenylphosphonium bromide (4.21 g, 11.8 mmol) was added to a stirred solution of potassium t-butoxide (1.26 g, 11.2 mmol) in 20 ml dry THF under a nitrogen atmosphere. The yellow suspension was stirred for 45 minutes at room temperature. A solution of (7α,17β)-7-methyl-3-keto-estr-5(10)-en-17-ol (3.4 g, 11.8 mmol) in 25 ml dry THF was added rapidly to the suspension. The yellow reaction mixture was stirred for 30 minutes at room temperature, poured on ice-water and extracted with ethyl acetate. The organic layer was washed with water, dried (Na2SO4) and evaporated to dryness to give 5.3 g of the title compound as a yellow oil. Column chromatography using toluene/ethyl acetate 95/5 (v/v %) as eluent gave 2.3 g of a colorless oil. Crystallization using heptane/petroleum ether gave (7α,17β)-7-methyl-3-methyleneestr-5(10)-en-17-ol (1.47 g, 44%) as a white solid, mp 111.8° C.

Workup

  1. stirringThe yellow reaction mixture was stirred for 30 minutes at room temperature
  2. additionpoured on ice-water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-eb3168d75e2040e2b864eb5f31720ef8
Source dataset
uspto-grants-2003_06
Patent number
US06579864B1

Reaction notes

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