Methanol → 21-Butyryl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

HRID 1973717ノート

反応式

HRID 1973717 の反応式
[C:1](OCC)(=[O:5])[CH2:2][CH2:3][CH3:4].[OH:9][C@@H:10]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:26]2[C:25](=[O:31])[CH2:24][C@@:23]2([CH3:32])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C:20](=[O:22])[CH3:21])[CH2:11]1.[H-].[Na+].CO>CS(C)=O>[C:1]([CH2:21][C:20](=[O:22])[C@@H:19]1[C@:23]2([CH3:32])[C@H:16]([C@H:15]3[C@H:26]([C:25](=[O:31])[CH2:24]2)[C@:27]2([CH3:30])[C@H:12]([CH2:11][C@H:10]([OH:9])[CH2:29][CH2:28]2)[CH2:13][CH2:14]3)[CH2:17][CH2:18]1)(=[O:5])[CH2:2][CH2:3][CH3:4]

参加物

6

反応物 4

HCID 887MethanolHCID 7762Ethyl butyrateHCID 24758Sodium hydrideHCID 104845Alphaxalone

生成物 1

HCID 8673428421-Butyryl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Ethyl butyrate (0.84 ml) was added to a mixture of 3α-hydroxy-5α-pregnane-11,20-dione (665 mg) and sodium hydride (150 mg.) in dry dimethyl sulphoxide (10 ml.). The mixture was stirred, under N2, for 13/4 hrs. The reaction mixture was treated with methyl alcohol to destroy excess sodium hydride, then poured into 2N-hydrochloric acid. The product was extracted with ethyl acetate and the combined extracts were washed with water, dried and evaporated. Preparative t.l.c. of the residue (859 mg.) gave two fractions. The more polar fraction was title compound (244 mg.) [α]D + 74.0°, λmax. 278 nm (ε 12,980).

後処理

  1. customto destroy excess sodium hydride
  2. additionpoured into 2N-hydrochloric acid
  3. extractionThe product was extracted with ethyl acetate
  4. washthe combined extracts were washed with water
  5. customdried
  6. customevaporated
  7. customof the residue (859 mg.) gave two fractions

出典と根拠

ORDレコード
ord-04599ae8fc9c42da9ae36406e75c1e56
出典データセット
uspto-grants-1976_12
特許番号
US03998829

反応ノート

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