{4-[2-(4-Benzyloxy-phenyl)-ethyl]-2-methyl-4,5-dihydro-oxazol-4-yl}-methanol → 4-[2-(4-Hydroxymethyl-2-methyl-4,5-dihydro-oxazol-4-yl)-ethyl]-phenol

HRID 490062Notes

Reaction equation

HRID 490062 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]2([CH2:23][OH:24])[CH2:21][O:20][C:19]([CH3:22])=[N:18]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:24][CH2:23][C:17]1([CH2:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[CH2:21][O:20][C:19]([CH3:22])=[N:18]1

Participants

4

Reactant 1

HCID 67054626{4-[2-(4-Benzyloxy-phenyl)-ethyl]-2-methyl-4,5-dihydro-oxazol-4-yl}-methanol

Product 1

HCID 579352584-[2-(4-Hydroxymethyl-2-methyl-4,5-dihydro-oxazol-4-yl)-ethyl]-phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of {4-[2-(4-benzyloxy-phenyl)-ethyl]-2-methyl-4,5-dihydro-oxazol-4-yl}-methanol (26.1 g, 0.08 mol) in methanol (800 ml) is added palladium on charcoal (2.6 g, 10% wt), and the reaction mixture is stirred under hydrogen atmosphere at RT for 5 hours. The reaction mixture is then filtered through celite and concentrated under vacuum. (R/S)-4-[2-(4-Hydroxymethyl-2-methyl-4,5-dihydro-oxazol-4-yl)-ethyl]-phenol is isolated in quantitative yield after crystallization with ethyl acetate and hexanes.

Workup

  1. filtrationThe reaction mixture is then filtered through celite
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9db73c301c4948b8801989ec2667a104
Source dataset
uspto-grants-2009_05
Patent number
US07528120B2

Reaction notes

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