3-Hydroxybenzaldehyde → 3-(2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy)benzaldehyde

HRID 1634068Notes

Reaction equation

HRID 1634068 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][OH:15].O[C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[O:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>ClCCl.CCCCCC>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[O:21]

Participants

7

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanol

Product 1

HCID 108046523-(2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy)benzaldehydeYield 84.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

2-(5-methyl-2-phenyloxazol-4-yl)ethanol (1.02 g), 3-hydroxybenzaldehyde (0.73 g) and triphenylphosphine (1.57 g) were dissolved in dichloromethane (10 ml) and thereto was added 1,1′(azodicarbonyl)dipiperidine (1.74 g) at 0° C. and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added hexane and the solid was filtered off. The filtrate was concentrated. The residue was purified by column chromatography on silica gel (methanol:chloroform=1:100) to give the title compound (1.30 g) having the following physical data.

Workup

  1. filtrationthe solid was filtered off
  2. concentrationThe filtrate was concentrated
  3. customThe residue was purified by column chromatography on silica gel (methanol:chloroform=1:100)

Sources & evidence

ORD record
ord-4df2d735b7ee42eebf2fc943aea3c09b
Source dataset
uspto-grants-2003_01
Patent number
US06506757B1

Reaction notes

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