3-Hydroxybenzyl alcohol → (3-{[2-(2-Furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}phenyl)methanol

HRID 2221508노트

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HRID 2221508 반응식
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].[OH:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][OH:19].C(=O)([O-])[O-].[K+].[K+].CN(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:14][C:15]2[CH:16]=[C:17]([CH2:18][OH:19])[CH:20]=[CH:21][CH:22]=2)[N:4]=1

참가 물질

6

반응물 4

HCID 1023-Hydroxybenzyl alcoholHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 223445824-(Chloromethyl)-2-(furan-2-yl)-5-methyl-1,3-oxazole

생성물 1

HCID 69217134(3-{[2-(2-Furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}phenyl)methanol수율 55.5%

시약·촉매·용매 1

HCID 962Water용매

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온도
90 °C

실험 절차

A mixture of 4-chloromethyl-2-(2-furyl)-5-methyl-1,3-oxazole (22.3 g), 3-hydroxybenzyl alcohol (10.0 g), potassium carbonate (11.14 g) and N,N-dimethylformamide (200 mL) was stirred at 90° C. for 4 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (1:1, v/v) to give (3-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}phenyl)methanol as colorless crystals (12.75 g, yield 55%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 100-101° C.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with ethyl acetate-hexane (1:1

출처 및 근거

ORD 기록
ord-b1eca34375a54c12a89819457556ad6d
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07368578B2

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