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

HRID 542229

反応式

HRID 542229 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-caf1133566164e30834c0c7c92913eaf
出典データセット
uspto-grants-1987_04
特許番号
US04656190

関連ノート

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