Methanol → HCID 54410002, compound

HRID 1584329Notes

Reaction equation

HRID 1584329 reaction equation
CO.C[O-].[Na+].[CH3:6][O:7][C:8]([CH2:10]P(OC)(OC)=O)=[O:9].[CH2:17]([O:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[O:28][CH2:29][C:30]1[N:31]=[C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:33][CH:34]=1)[CH:23]=O)[CH3:18]>CN(C)C=O>[CH2:17]([O:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[O:28][CH2:29][C:30]1[N:31]=[C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:33][CH:34]=1)[CH:23]=[CH:10][C:8]([O:7][CH3:6])=[O:9])[CH3:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 80029Trimethyl phosphonoacetateHCID 10942334Sodium MethoxideHCID 21224499HCID 21224499, compound

Product 1

HCID 54410002HCID 54410002, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A methanol solution of sodium methoxide (28%, 3.4 g) was added dropwise to an ice-cooled solution of trimethyl phosphonoacetate (3.2 g) and 3-ethoxy-4-(2-phenyl-4-oxazolylmethoxy)benzaldehyde (5.1 g) in N,N-dimethylformamide (DMF) (30 ml). The mixture was stirred for 5 minutes under ice-cooling, then for 4 hours at room temperature. The reaction mixture was poured into ice-water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated to yield methyl 3-ethoxy-4-(2-phenyl-4-oxazolylmethoxy)cinnamate (5.5 g, 91%), which was recrystallized from chloroform-ether to give colorless prisms, m.p.125-126° C.

Workup

  1. temperaturecooling
  2. waitfor 4 hours at room temperature
  3. extractionwas subjected to extraction with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-acdc1b1c1e8443a7963e6673b20b2291
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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