Dimethylformamide → HCID 86591669, compound

HRID 1295217Notes

Reaction equation

HRID 1295217 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[O:6][C:7]=1[CH3:8].C(O[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)(=O)C.[C:26](=[O:29])([O-])[O-:27].[K+].[K+].[CH3:32]N(C)C=O>O>[O:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[C:5]1[O:6][C:7]([CH3:8])=[C:3]([CH2:2][O:25][C:22]2[CH:21]=[CH:20][C:19]([CH2:18][C:26]([O:27][CH3:32])=[O:29])=[CH:24][CH:23]=2)[N:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11788491HCID 11788491, compoundHCID 223445824-(Chloromethyl)-2-(furan-2-yl)-5-methyl-1,3-oxazole

Product 1

HCID 86591669HCID 86591669, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-chloromethyl-2-(2-furyl)-5-methyloxazole (10.0 g), 4-hydroxyphenylmethyl acetate (8.41 g), potassium carbonate (14.0 g) and N,N-dimethylformamide (50 ml) was stirred at 70° C. for 1 hr. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and methyl [4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]phenyl]acetate (9.23 g, yield 56%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (2:3, volume ratio).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a545c6c61de844d3bc3ee4d041a8ed0a
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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