Water → Methyl 2-(2-(benzyloxy)phenyl)-3-methoxyacrylate

HRID 1086993

반응식

HRID 1086993 반응식
[OH:1][CH:2]=[C:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:4]([O:6][CH3:7])=[O:5].[C:22](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.O>CN(C=O)C>[CH3:22][O:1]/[CH:2]=[C:3](\[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)/[C:4]([O:6][CH3:7])=[O:5].[CH2:15]([O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:3][C:4]([O:6][CH3:7])=[O:5])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 69942437Methyl 2-(2'-benzyloxyphenyl)-3-hydroxyacrylate

생성물 2

HCID 838698Methyl 2-(2-(benzyloxy)phenyl)-3-methoxyacrylateHCID 11076055Methyl 2-(2-(benzyloxy)phenyl)acetate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

The crude methyl 3-hydroxy-2-(2'-benzyloxyphenyl)propenoate was dissolved in dry DMF (100 ml) and potassium carbonate (29.0 g) was added in one portion. Dimethyl sulphate (16.00 g) in dry DMF (10 ml) was then added dropwise with stirring. After ninety minutes, water (300 ml) was added and the solution was extracted with ether (2 x 300 ml). After washing with water (3 x 150 ml) and brine, the extracts were dried and concentrated under reduced pressure, and the resulting yellow oil solidified on trituration with ether/petrol. Recrystallization from dry methanol afforded E-methyl 3-methoxy-2-(2'-benzyloxyphenyl)propenoate as a white, crystalline solid (5.44g, 17% yield from methyl 2-benzyloxyphenylacetate), M.P. 76-77° C.; infrared maxima (nujol mull): 1710, 1640 cm-1 ; 1H nmr (CDCl3, 90MHz): delta 3.63 (3H,s), 3.75 (3H,s), 5.05 (2H,s), 6.80-7.40 (9H,m), 7.50 (1H,s)ppm.

후처리

  1. waitAfter ninety minutes
  2. extractionthe solution was extracted with ether (2 x 300 ml)
  3. washAfter washing with water (3 x 150 ml) and brine
  4. customthe extracts were dried
  5. concentrationconcentrated under reduced pressure
  6. customRecrystallization from dry methanol

출처 및 근거

ORD 기록
ord-a1c0d762440c4a9c8b15d14b0891577c
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05034388

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