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

HRID 345273
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HRID 345273 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](=[CH:20][OH:21])[C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1/[C:15](=[CH:20]\[O:21][CH3:22])/[C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

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 2-(2'-benzyloxyphenyl)-3-hydroxyacrylate 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 (2×300 ml). After washing with water (3×150 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 2-(2'-benzyloxyphenyl)-3-methoxyacrylate as a white, crystalline solid (5.44 g, 17% yield from methyl 2-benzyloxyphenylacetate), mp. 76°-77° C.; infrared max. (nujol mull): 1710, 1640 cm-1 ; 1H nmr (90 MHz): 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 (2×300 ml)
  3. washAfter washing with water (3×150 ml) and brine
  4. customthe extracts were dried
  5. concentrationconcentrated under reduced pressure
  6. customRecrystallization from dry methanol

출처 및 근거

ORD 기록
ord-5d6854c7bffd489589e7614b757f57ba
출처 데이터셋
uspto-grants-1991_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05057146

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