Vanillin → HCID 21224400, compound

HRID 1584364Notes

Reaction equation

HRID 1584364 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH3:13][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[CH:25]([OH:27])[CH3:26].[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:37]=[O:38])[CH:33]=[CH:34][C:35]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:33]=[CH:34][C:35]=1[O:27][CH: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[CH3:13])[CH3:26])[CH:37]=[O:38]

Participants

6

Reactant 4

HCID 1183VanillinHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 184738961-(5-Methyl-2-phenyl-4-oxazolyl)ethanol

Product 1

HCID 21224400HCID 21224400, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (DEAD) (4.71 g) was added dropwise, under ice-cooling, to a mixture of 1-(5-methyl-2-phenyl-4-oxazolyl)ethanol (5.0 g), vanilline (3.75 g), triphenylphosphine (Ph3P) (7.1 g) and tetrahydrofuran (THF) (80 ml). The reaction mixture was stirred for 8 hours at room temperature and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate-hexane (1:4, v/v), was obtained 3-methoxy-4-[1-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzaldehyde (4.48 g, 54%), which was recrystallized from ethyl acetate-hexane to give colorless needles, m.p.104-105° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washFrom the fraction eluted with ethyl acetate-hexane (1:4, v/v)

Sources & evidence

ORD record
ord-f40cb074535f4aed894cfd10a05baaea
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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