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

HRID 649744

反応式

HRID 649744 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-1c064eb3c71342cebdb773f9121df67f
出典データセット
uspto-grants-2001_08
特許番号
US06271220B1

関連ノート

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