Sodium hydride → HCID 21967810、化合物

HRID 1003185ノート

反応式

HRID 1003185 の反応式
C([O:4][C:5]1[C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14](=[O:27])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)(=O)C.[H-].[Na+]>C1COCC1.CO>[OH:4][C:5]1[C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14](=[O:27])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1

参加物

5

反応物 2

HCID 24758Sodium hydrideHCID 21967809HCID 21967809、化合物

生成物 1

HCID 21967810HCID 21967810、化合物収率 87.1%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 3-acetoxyestra-1,3,5(10)-trien-17-one-2-carboxylate (63, 0.746 g, 2.0 mmol) in THF (10 mL) and MeOH (15 mL) was added sodium hydride (0.240 g of a mineral oil dispersion, 60%, 6.0 mmol) at 0° C. The reaction mixture was stirred for 30 min, and quenched with saturated aqueous NH4Cl at 0° C., and extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl, and then dried (Na2SO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was purified by column chromatography (silica gel) using n-hexane:EtOAc (3:1, v/v) to afford 0.572 g of 64 (87% yield) mp: 178-179° C.

後処理

  1. customquenched with saturated aqueous NH4Cl at 0° C.
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with H2O, saturated aqueous NaCl
  4. dry with materialdried (Na2SO4)
  5. filtrationThe desiccant was filtered
  6. customthe solvent was evaporated at reduced pressure
  7. customThe residue was purified by column chromatography (silica gel)

出典と根拠

ORDレコード
ord-6a46bd4cca574b318f9412302e6b827c
出典データセット
uspto-grants-2000_04
特許番号
US06046186

反応ノート

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