Methyl (5-fluoro-2-methyl-1H-inden-3-yl)acetate → 5-fluoro-2-methyl-1H-3-indenyl-(2-hydroxy) ethane

HRID 542229

반응식

HRID 542229 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([CH3:11])=[C:5]2[CH2:12][C:13](OC)=[O:14].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([CH3:11])=[C:5]2[CH2:12][CH2:13][OH:14]

참가 물질

4

반응물 2

HCID 15434585Methyl (5-fluoro-2-methyl-1H-inden-3-yl)acetateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 139332935-fluoro-2-methyl-1H-3-indenyl-(2-hydroxy) ethane수율 71.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 14b (24 g) in dry THF (300 ml), LiAlH4 (6.9 g) was added in portions. The mixture was stirred at room temperature for 1.5 hours. Excess LiAlH4 (LAH) was destroyed with saturated Na2SO4 solution. The organic phase was concentrated in vacuo, and the crude product was purified via silica gel column chromatography eluting with methylene chloride. The product was recrystallized from hexane to give 5-fluoro-2-methyl-1H-3-indenyl-(2-hydroxy)ethane (15b) (14.9 g, 63% yield): m.p. 65°-66.5° C.

후처리

  1. customExcess LiAlH4 (LAH) was destroyed with saturated Na2SO4 solution
  2. concentrationThe organic phase was concentrated in vacuo
  3. customthe crude product was purified via silica gel column chromatography
  4. washeluting with methylene chloride
  5. customThe product was recrystallized from hexane

출처 및 근거

ORD 기록
ord-caf1133566164e30834c0c7c92913eaf
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04656190

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