Sodium borohydride → 1-{6-[4-(Trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol

HRID 1391727ノート

反応式

HRID 1391727 の反応式
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([C:15](=[O:20])[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+]>C1COCC1.O>[F:21][C:2]([F:1])([F:22])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[C:13]([CH:15]([OH:20])[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 586299011-{6-[4-(Trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanone

生成物 1

HCID 586298221-{6-[4-(Trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol収率 99.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanone (2.80 g, 9.11 mmol) in THF (61 mL) at 0° C. (ice/water bath) was treated drop-wise with a mixture of sodium borohydride (689 mg, 18.21 mmol) in water (11 mL) over 5-10 minutes. The resulting mixture was stirred at this temperature for 2.5 hours and was then partitioned between EtOAc (200 mL) and water (200 mL) and the layers separated. The aqueous was re-extracted with EtOAc (200 mL) and the combined organic layer washed with brine (250 mL), dried (MgSO4), filtered and reduced. Purification by Biotage™ chromatography (silica) eluting with cyclohexane:EtOAc (gradient 20:1 to 5:1) afforded the title compound as a colourless oil (2.81 g).

後処理

  1. additionwas treated drop-wise
  2. customwas then partitioned between EtOAc (200 mL) and water (200 mL)
  3. customthe layers separated
  4. extractionThe aqueous was re-extracted with EtOAc (200 mL)
  5. washthe combined organic layer washed with brine (250 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customPurification by Biotage™ chromatography (silica)
  9. washeluting with cyclohexane

出典と根拠

ORDレコード
ord-beda19d4626a4e8c874d260255c78966
出典データセット
uspto-grants-2008_03
特許番号
US07338960B2

反応ノート

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