Equilin → 17-Methylenestra-1,3,5(10),7-tetraen-3-ol

HRID 1781946노트

반응식

HRID 1781946 반응식
[CH3:1]C(C)([O-])C.[K+].[CH3:7][C@@:8]12[C:24](=O)[CH2:23][CH2:22][C@H:21]1[C:20]1[C@@H:11]([C:12]3[CH:13]=[CH:14][C:15]([OH:26])=[CH:16][C:17]=3[CH2:18][CH:19]=1)[CH2:10][CH2:9]2>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CS(C)=O>[CH2:1]=[C:24]1[CH2:23][CH2:22][C@H:21]2[C:20]3[C@H:11]([CH2:10][CH2:9][C@:8]12[CH3:7])[C:12]1[CH:13]=[CH:14][C:15]([OH:26])=[CH:16][C:17]=1[CH2:18][CH:19]=3

참가 물질

5

반응물 2

HCID 223368EquilinHCID 23665647Potassium tert-butoxide

생성물 1

HCID 2287307017-Methylenestra-1,3,5(10),7-tetraen-3-ol

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 679Dimethyl Sulfoxide용매2회

실험 절차

Methyltriphenylphosphonium bromide (1.9967 g, 5.5892 mmol) and potassium t-butoxide (627.2 mg, 5.589 mmol) suspended in 6.1 mL of anh. DMSO under argon were 1 h in an oil bath (71°-83° C., after which equilin (300.0 mg, 1.118 mmol) in 6.1 μL of anh. DMSO was added via syringe. See FIG. 18. After stirring a further 70 min., the reaction mixture was poured into 40 mL of ice water and extracted three times with 25 mL portions of ether. The combined organic extracts were washed with 25 mL of brine, dried over magnesium sulfate, and filtered through diatomaceous earth. The residue was washed with 10 mL of ether and the combined filtrates were concentrated under reduced pressure. Flash chromatography (15% ethyl acetate/hexanes on silica gel) followed by preparative TLC (20% ethyl acetate/hexanes on silica gel GF, 1000μ thickness) gave an opaque white film (162.3 mg, 0.6093 mmol, 54%). (NA)-1994A-258)

후처리

  1. extractionextracted three times with 25 mL portions of ether
  2. washThe combined organic extracts were washed with 25 mL of brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered through diatomaceous earth
  5. washThe residue was washed with 10 mL of ether
  6. concentrationthe combined filtrates were concentrated under reduced pressure
  7. customgave an opaque white film (162.3 mg, 0.6093 mmol, 54%)

출처 및 근거

ORD 기록
ord-0e8369bf0a9a4d91adb66baad07b17e0
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05633392

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