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

HRID 1348685Notes

Reaction equation

HRID 1348685 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-b70b67b863da42a6b7ef3cbba980b84d
Source dataset
uspto-grants-2007_05
Patent number
US07211591B2

Reaction notes

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