Sodium borohydride → {4-[1-(4-trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]-phenyl}-methanol

HRID 1038307

反応式

HRID 1038307 の反応式
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[BH4-].[Na+]>CCO.CCOC(C)=O>[F:24][C:2]([F:1])([F:23])[O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:22]=[CH:21][C:18]([CH2:19][OH:20])=[CH:17][CH:16]=3)=[N:11]2)=[CH:8][CH:9]=1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 578244624-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzaldehyde

生成物 1

HCID 66776992{4-[1-(4-trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]-phenyl}-methanol収率 93%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4-[1-(4-trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]-benzaldehyde (P-3; 2.59 g, 7.79 mmol) in EtOH (120 mL), sodium borohydride (725.8 mg, 19.18 mmol) was added as a solid in portions at room temperature. After the addition was complete, the mixture was stirred at room temperature for 90 minutes (min). The mixture was then diluted with EtOAc and washed with H2O. The aqueous fraction was extracted with EtOAc. The organic fractions were combined, dried over anhydrous MgSO4, and evaporated at room temperature under vacuum. The crude material was absorbed to silica gel with EtOAc and eluted with 50% EtOAc in hexane. The title product (2.43 g, 93%) was isolated as a white solid: mp 112-114° C.; 1H NMR (300 MHz, CDCl3) δ 8.55 (s, 1H), 8.29-8.12 (m, 2H), 7.91-7.69 (m, 2H), 7.43 (ddd, J=9.0, 5.7, 4.5 Hz, 4H), 4.78 (d, J=6.0 Hz, 2H), 2.07 (t, J=6.0 Hz, 1H); ESIMS m/z 336 (M+H).

後処理

  1. additionAfter the addition
  2. washwashed with H2O
  3. extractionThe aqueous fraction was extracted with EtOAc
  4. dry with materialdried over anhydrous MgSO4
  5. customevaporated at room temperature under vacuum
  6. customThe crude material was absorbed to silica gel with EtOAc
  7. washeluted with 50% EtOAc in hexane

出典と根拠

ORDレコード
ord-da93391a4e8a4b1eba5bde6f37aad3b6
出典データセット
uspto-grants-2013_10
特許番号
US08551914B2

関連ノート

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