Sodium hydride → 2-Chloro-7-(3-chloro-4-methoxy-phenyl)-5-cyclopentyl-5-hydroxy-3-oxo-heptanoic acid methyl ester

HRID 1453302노트

반응식

HRID 1453302 반응식
[CH3:1][O:2][C:3](=[O:9])[CH:4]([Cl:8])[C:5]([CH3:7])=[O:6].[H-].[Na+].[Li]CCCC.[Cl:17][C:18]1[CH:19]=[C:20]([CH2:26][CH2:27][C:28]([CH:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[O:29])[CH:21]=[CH:22][C:23]=1[O:24][CH3:25]>C1COCC1>[CH3:1][O:2][C:3](=[O:9])[CH:4]([Cl:8])[C:5](=[O:6])[CH2:7][C:28]([CH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)([OH:29])[CH2:27][CH2:26][C:20]1[CH:21]=[CH:22][C:23]([O:24][CH3:25])=[C:18]([Cl:17])[CH:19]=1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 107332Methyl 2-chloroacetoacetateHCID 219385963-(3-Chloro-4-methoxy-phenyl)-1-cyclopentyl-propan-1-oneHCID 178418339Butyllithium

생성물 1

HCID 210622722-Chloro-7-(3-chloro-4-methoxy-phenyl)-5-cyclopentyl-5-hydroxy-3-oxo-heptanoic acid methyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-40 °C

실험 절차

Methyl-2-chloroacetoacetate (2.5 g, 16.9 mmol) was added to a cooled 0° C. suspension of NaH (0.68 g, 16.9 mmol, 60% dispersion in mineral oil) in THF (30 ml). After 15 min the solution was cooled to −40° C. and n-BuLi (10.6 mL, 16.9 mmol, 1.6M in hexanes) was added. The resulting dianion was stirred for an additional 30 min and then treated with a solution of 3-(3-Chloro-4-methoxy-phenyl)-1-cyclopentyl-propan-1-one (1.5 g, 5.6 mmol, prepared from Heck route) in THF (10 ml). After stirring for 1H at −40° C., the reaction mixture was quenched with saturated NH4Cl and extracted with EtOAc. The organic layers were washed with brine, dried with Na2SO4 and concentrated to an orange oil that was used without further purification.

후처리

  1. stirringAfter stirring for 1H at −40° C.
  2. customthe reaction mixture was quenched with saturated NH4Cl
  3. extractionextracted with EtOAc
  4. washThe organic layers were washed with brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated to an orange oil that
  7. customwas used without further purification

출처 및 근거

ORD 기록
ord-f783c27b59504e158ccfc050983c62db
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473790B2

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