Benzophenone → 2(1-Methyltetrazol-5-yl)-1,1-diphenylethanol

HRID 1195389

反応式

HRID 1195389 の反応式
[CH3:1][N:2]1[C:6]([CH3:7])=[N:5][N:4]=[N:3]1.C([Li])CCC.[C:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[CH3:1][N:2]1[C:6]([CH2:7][C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[OH:20])=[N:5][N:4]=[N:3]1

参加物

5

反応物 3

HCID 3102BenzophenoneHCID 788251,5-DimethyltetrazoleHCID 178418339Butyllithium

生成物 1

HCID 147240362(1-Methyltetrazol-5-yl)-1,1-diphenylethanol収率 22%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

A solution of 1,5-dimethyltetrazole (20 g; 0.204 mole) in dry THF (200 mL) was cooled to -78° C. and treated with n-butyllithium (91 mL of 2.5 molar solution in hexane; 0.227 mole) and the mixture stirred at -78° C. for 30 minutes. Benzophenone (31.1 g; 0.171 mole) was added and the mixture stirred at -78° C. for 30 minutes and allowed to warm up to 23° C. and stirred for 15 hours. The mixture was quenched with 2N HCl (100 mL) and extracted with EtOAc (3×150 mL). The combined organic layers were dried (MgSO4) and evaporated. The residue was crystallized from EtOAc-Hexane to afford the title compound as a white solid (10.5 g; 22%); m.p.=175°-176° C. (crystallized from EtOAc-hexane). MS (CI): m/e=281 for (M+H)+.

後処理

  1. stirringthe mixture stirred at -78° C. for 30 minutes
  2. temperatureto warm up to 23° C.
  3. stirringstirred for 15 hours
  4. customThe mixture was quenched with 2N HCl (100 mL)
  5. extractionextracted with EtOAc (3×150 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. customevaporated
  8. customThe residue was crystallized from EtOAc-Hexane

出典と根拠

ORDレコード
ord-4b1e4e7f20a04934a64030117cf3c3fc
出典データセット
uspto-grants-1992_05
特許番号
US05110940

関連ノート

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