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

HRID 1450156

反応式

HRID 1450156 の反応式
[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

参加物

7

反応物 4

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-39baa328488a4f06a95cf95f93db7760
出典データセット
uspto-grants-1997_02
特許番号
US05602076

関連ノート

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