Sodium hydride → HCID 21967810, 화합물

HRID 1003185노트

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HRID 1003185 반응식
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

참가 물질

5

반응물 2

HCID 24758Sodium hydrideHCID 21967809HCID 21967809, 화합물

생성물 1

HCID 21967810HCID 21967810, 화합물수율 87.1%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6a46bd4cca574b318f9412302e6b827c
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06046186

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