Sodium borohydride → [6-[2-(3-Methoxypropyl)phenyl]-4-(trifluoromethyl)pyridin-3-yl]methanol

HRID 2194897ノート

反応式

HRID 2194897 の反応式
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[C:15]([C:16](OC)=[O:17])=[CH:14][N:13]=1.[BH4-].[Na+]>CO.O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:13]=[CH:14][C:15]([CH2:16][OH:17])=[C:20]([C:22]([F:23])([F:25])[F:24])[CH:21]=1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 67447798Methyl 6-[2-(3-methoxypropyl)phenyl]-4-(trifluoromethyl)nicotinate

生成物 1

HCID 67448255[6-[2-(3-Methoxypropyl)phenyl]-4-(trifluoromethyl)pyridin-3-yl]methanol

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
65 °C

実験手順

To a solution of methyl 6-[2-(3-methoxypropyl)phenyl]-4-(trifluoromethyl)nicotinate (1 eq.) from step 1, in MeOH (0.14M) was added portion wise sodium borohydride (9.3 eq.). The mixture was stirred at 65° C. for 12 h, cooled to room temperature, poured in water and extracted with EtOAc. The organic extract was washed with brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel, eluting with Hex/EtOAc 20% afforded the desired compound as an oil.

後処理

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography on silica gel
  9. washeluting with Hex/EtOAc 20%

出典と根拠

ORDレコード
ord-709134f9f9724bd6b5db0381c8e33ee6
出典データセット
uspto-grants-2012_12
特許番号
US08334308B2

反応ノート

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