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

HRID 8971

반응식

HRID 8971 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 207256244-(Oxazol-2-yl)-benzyl alcohol수율 89%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-85cb7c3d3f1440a8a446dd9990ca3e2b
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091217B2

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