Methanol → 5-(trifluoromethyl)-2,3-dihydro-1H-inden-1-ol

HRID 2178768ノート

反応式

HRID 2178768 の反応式
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.[BH4-].[Na+].CO>C1COCC1>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([OH:12])[CH2:7][CH2:6]2

参加物

5

反応物 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 121749875-(Trifluoromethyl)indan-1-one

生成物 1

HCID 248204735-(trifluoromethyl)-2,3-dihydro-1H-inden-1-ol収率 107.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5-(trifluoromethyl)indan-1-one (0.7 g, 3 mmol) in THF (5 mL) cooled in an ice bath was added sodium borohydride (0.1 g, 3 mmol) followed by MeOH (1 mL). After being stirred for 30 min, the reaction was quenched with aqueous NaHCO3. The resulting solution was extracted with EtOAc twice. The extracts were washed with brine, dried (MgSO4), filtered and concentrated. The crude material was purified by flash chromatography on silica eluting with 20% EtOAc/hexane to afford the desired product (0.65 g, 92%) as an oil. LC/MS calculated for C10H9F3O: (M+H)+203; found 185.1 (M+H—H2O)+.

後処理

  1. customthe reaction was quenched with aqueous NaHCO3
  2. extractionThe resulting solution was extracted with EtOAc twice
  3. washThe extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography on silica eluting with 20% EtOAc/hexane

出典と根拠

ORDレコード
ord-4e80906e6f7e4d768ab505c9ece95f6e
出典データセット
uspto-grants-2015_06
特許番号
US09067921B2

反応ノート

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