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

HRID 8971

Reaction equation

HRID 8971 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-85cb7c3d3f1440a8a446dd9990ca3e2b
Source dataset
uspto-grants-2006_08
Patent number
US07091217B2

Linked notes

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