Diisobutylaluminum hydride → (4-Methyl-2-phenyl-1,3-oxazol-5-yl)methanol

HRID 2230899Notes

Reaction equation

HRID 2230899 reaction equation
CC(C[AlH]CC(C)C)C.C[O:11][C:12]([C:14]1[O:18][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:16][C:15]=1[CH3:25])=O>C1(C)C=CC=CC=1.C1COCC1>[CH3:25][C:15]1[N:16]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:18][C:14]=1[CH2:12][OH:11]

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 3310118methyl 4-methyl-2-phenyl-1,3-oxazole-5-carboxylate

Product 1

HCID 23438974(4-Methyl-2-phenyl-1,3-oxazol-5-yl)methanol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

19.0 mL of 1.0 M DIBAL-H solution in toluene is added slowly to a solution of 1.63 g (7.5 mmol) of 4-methyl-2-phenyl-oxazole-5-carboxylic acid methyl ester (J. Chem. Soc., Chem. Comm. 1995, 22, 2335) in 30 mL of THF at −78° C. The cooling bath is removed, and the reaction mixture is stirred overnight. The reaction mixture is cooled to −78° C. and quenched with 9 mL of MeOH. The cooling bath is removed, and 9 mL of brine and 6.5 g of Na2SO4 are added, and the reaction mixture is stirred vigorously for 2 h, and then filtered off, and concentrated in vacuo to produce (4-methyl-2-phenyl-oxazol-5-yl)-methanol as a solid; 1H NMR (250 MHz, CDCl3) δ7.93-8.01 (m, 2H), 7.37-7.43 (m, 3H), 4.65 (s, 2H), 2.61 (br, s, 1H), 2.18 (s, 3H).

Workup

  1. customThe cooling bath is removed
  2. customquenched with 9 mL of MeOH
  3. customThe cooling bath is removed
  4. addition9 mL of brine and 6.5 g of Na2SO4 are added
  5. stirringthe reaction mixture is stirred vigorously for 2 h
  6. filtrationfiltered off
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56a2cf35524244579b773b348d9a15c9
Source dataset
uspto-grants-2002_07
Patent number
US06426354B1

Reaction notes

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