Tetrahydrofuran → 3-Methoxyestra-3,5(10)-dien-17beta-ol

HRID 649744

반응식

HRID 649744 반응식
[CH3:1][O:2][C:3]1[CH2:4][C:5]2[CH2:6][CH2:7][C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]1[OH:21].O1CCCC1.CC([O-])(C)C.[K+]>CS(C)=O>[CH3:1][O:2][C:3]1[CH2:20][CH2:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@@H:12]([OH:21])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 1019633-Methoxyestra-2,5(10)-dien-17beta-olHCID 23665647Potassium tert-butoxide

생성물 1

HCID 106133673-Methoxyestra-3,5(10)-dien-17beta-ol수율 65.3%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

3-Methoxyestra-2,5(10)-dien-17β-ol 1 (2.0 g, 6.9 mmol) was added to a solution consisting of tetrahydofuran (15 ml), DMSO (5 ml) and t-BuOK (20.7 mmol). The resultant solution was stirred at ambient temperature for 10 hours at which time the solution was concentrated to Å5 ml and chromatographically filtered with 50% ethylether/petroleum ether (light) through 10 g of silica gel. The subsequent dimethyl sulfoxide (DMSO) free -powder was flash chromatographed affording 4 as white needles (1.30 g, 65% conversion, 91% based on recovered 1), Alternatively, crystallization by selective seeding (ether/methanol) was utilized, thereby circumventing chromatographic purification. 1H NMR (d6-acetone) δ4.629 (s, 1H), 3.505 (t, J=8.09 Hz, 1H), 3.431 (s, 3H), 2.15-0.98 (complex, 20H), 0.644 (s, 3H). 13C NMR (CDCl3) δ156.71, 126.56, 123.88, 96.55, 81.31, 54.19, 50.18, 46.03, 39.91, 37.54, 30.64, 30.58, 30.21, 27.71, 27.17, 25.67, 25.24, 23.22, 11.37.

후처리

  1. concentrationwas concentrated to Å5 ml
  2. filtrationchromatographically filtered with 50% ethylether/petroleum ether (light) through 10 g of silica gel
  3. customchromatographed

출처 및 근거

ORD 기록
ord-1c064eb3c71342cebdb773f9121df67f
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06271220B1

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