Diisobutylaluminum hydride → 4-(Oxazol-2-yl)-benzyl alcohol

HRID 8971

反応式

HRID 8971 の反応式
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][CH:12]=[CH:13][N:14]=2)=[CH:6][CH:5]=1.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[O:11]1[CH:12]=[CH:13][N:14]=[C:10]1[C:7]1[CH:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=1

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 21985208Methyl 4-(oxazol-2-yl)benzoate

生成物 1

HCID 207256244-(Oxazol-2-yl)-benzyl alcohol収率 89%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of methyl-4-(oxazol-2-yl)-benzoate (0.203 g, 1 mmol) in CH2Cl2 (10 mL) 0° C. was added DIBAL-H (4 mL of a 1.0M solution in dichloromethane, 4 mmol) over 10 minutes. The resultant solution was stirred at 0° C. for 2 hours then quenched with an aqueous saturated solution of sodium potassium tartrate (20 mL) and the biphasic mixture stirred rapidly for 60 minutes. The phases were separated and the aqueous layer extracted with CH2Cl2 (3×10 mL). The combined organic fractions were dried (Na2SO4), filtered, concentrated and purified by chromatography on silica gel (10:1 CH2Cl2/MeOH) to afford the title alcohol (0.156 g, 89%). 1H NMR (CDCl3) δ 3.42 (t, 1H, J=6.0 Hz (OH)), 4.77 (s, 2H, J=6.0 Hz), 7.24 (s, 1H), 7.47 (d, 2H, J=7.8 Hz), 7.71 (s, 1H), 8.05 (d, 2H, J=7.8 Hz).

後処理

  1. customthen quenched with an aqueous saturated solution of sodium potassium tartrate (20 mL)
  2. customThe phases were separated
  3. extractionthe aqueous layer extracted with CH2Cl2 (3×10 mL)
  4. dry with materialThe combined organic fractions were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by chromatography on silica gel (10:1 CH2Cl2/MeOH)

出典と根拠

ORDレコード
ord-85cb7c3d3f1440a8a446dd9990ca3e2b
出典データセット
uspto-grants-2006_08
特許番号
US07091217B2

関連ノート

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