Water → (E)-methyl 2-(2-formylphenyl)-3-methoxypropenoate

HRID 1755656노트

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HRID 1755656 반응식
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11].P([O-])([O-])(O)=[O:18].[Na+].[Na+].P([O-])([O-])(O)=O.[K+].[K+].O>CS(C)=O>[CH:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11])=[O:18]

참가 물질

6

반응물 4

HCID 962WaterHCID 24203Sodium Phosphate, DibasicHCID 24450Potassium Phosphate, DibasicHCID 9925856(E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate

생성물 1

HCID 22872991(E)-methyl 2-(2-formylphenyl)-3-methoxypropenoate수율 40%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
80 °C

실험 절차

A mixture of (E)-methyl 2-[2-(bromomethyl)phenyl]-3-methoxypropenoate (10.0 g, 90% pure), sodium hydrogen orthophosphate dibasic (Na2HPO4, 5.74 g) and potassium hydrogen monophosphate monobasic (KH2PO4, 0.55 g) in DMSO (20 ml) was heated at 80° C. for 1 hour and then at 110° C. for a further hour (compare J. H. Babler, M. J. Coghlan, M. Feng and P. Fries, J. Org. Chem., 1979, 44, 1716). After cooling, the reaction mixture was poured into water and extracted with ether. The extracts were washed with brine, dried, concentrated and chromatographed using ether as eluant to give (E) -methyl 2-(2-formylphenyl)-3-methoxypropenoate (2.77 g, 40% yield) as a white crystalline solid, m.p. 67°-69° C. IR (nujol): 1710, 1634 cm-1. 1H NMR: delta 3.72 (3H, s), 3.84 (3H, s), 7.30-7.65 (3H, m), 7.69 (1H, s), 7.9 (1H, m), 10.0 (1H, s) ppm.

후처리

  1. waitat 110° C. for a further hour (compare J. H. Babler, M. J. Coghlan, M. Feng and P. Fries, J. Org. Chem., 1979, 44, 1716)
  2. temperatureAfter cooling
  3. extractionextracted with ether
  4. washThe extracts were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customchromatographed

출처 및 근거

ORD 기록
ord-c6f00cc89feb481aa2812793272c265f
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05438059

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