Water → HCID 69423813, compound

HRID 350153Notes

Reaction equation

HRID 350153 reaction equation
[CH3:1][C:2]1[C:6]([CH:7]=O)=[C:5]([CH3:9])[N:4]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[N:20]=[C:21]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[O:22][C:23]=3[CH3:24])=[CH:13][CH:12]=2)[N:3]=1.C(OP([CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])(OCC)=O)C.[H-].[Na+].O>CN(C)C=O>[CH3:1][C:2]1[C:6](/[CH:7]=[CH:39]/[C:40]([O:42][CH2:43][CH3:44])=[O:41])=[C:5]([CH3:9])[N:4]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]3[N:20]=[C:21]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[O:22][C:23]=3[CH3:24])=[CH:15][CH:16]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 23024995HCID 23024995, compound

Product 1

HCID 69423813HCID 69423813, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,5-dimethyl-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-carbaldehyde (900 mg) and ethyl diethylphosphonoacetate (1.10 g) in N,N-dimethylformamide (20 ml), sodium hydride (60%, oily, 200 mg) was added at 0, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated. The obtained crystals were collected by filtration, and ethyl(E)-3-[3,5-dimethyl-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propenoate (740 mg) was obtained. After the mother liquor was concentrated, the residue was subjected to silica gel column chromatography, and 150 mg of crystals were additionally obtained from the fraction eluted with ethyl acetate-hexane (2:3, volume ratio). The total was 890 mg (yield: 87%). This was recrystallized from ethyl acetate-isopropyl ether. Melting point: 98–99° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. filtrationThe obtained crystals were collected by filtration

Sources & evidence

ORD record
ord-653337b126f64299a97a3813764bbc1a
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

Loading…