Water → (E)-3-(2,4-dibenzyloxyphenyl)prop-2-enoic acid

HRID 322848

反応式

HRID 322848 の反応式
C([Li])CCC.[CH2:6]([C:8](CC)(P(O)(O)=O)[C:9]([OH:11])=[O:10])C.[CH2:18]([O:25][C:26]1[CH:33]=[C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:31]=[CH:30][C:27]=1C=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>O1CCCC1>[CH2:18]([O:25][C:26]1[CH:33]=[C:32]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:31]=[CH:30][C:27]=1/[CH:6]=[CH:8]/[C:9]([OH:11])=[O:10])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

6

反応物 4

HCID 962WaterHCID 18090802,4-Bis(benzyloxy)benzaldehydeHCID 17786294HCID 17786294、化合物HCID 178418339Butyllithium

生成物 1

HCID 10737234(E)-3-(2,4-dibenzyloxyphenyl)prop-2-enoic acid収率 36.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-70 °C

実験手順

To a solution of 2.5 M n-butyl lithium (3.64 mL) in dry tetrahydrofuran (THF) (20 mL) that is cooled to −70° C. under nitrogen is added a solution of diethyl phosphonoacetic acid (0.89 g) in THF (5 mL). After 30 minutes a solution of 2,4-dibenzyloxybenzaldehyde (1.46 g) in THF (5 mL) is slowly added to the cooled solution so as to maintain the temperature. The resulting mixture is stirred at −70° C. for 3 hours and then at 25° C. for 18 hours. The resulting suspension is treated with water, the THF is removed in vacuo,the residue is extracted with ethyl acetate, the extract is dried and evaporated. The residual solid is recrystallized from isopropanol to yield (E)-3-(2,4-dibenzyloxyphenyl)prop-2-enoic acid as colourless crystals (0.6 g), m.p. 153-155° C. H NMR (DMSO) 5.15 (2H,s), 5.21(2H,s), 6.4(1H,d,J=16 Hz), 6.7(1H,d), 6.85(1H,s), 7.3-7.5(10H,m), 7.6(1H,d), 7.8(1H,d,J=16 Hz).

後処理

  1. temperatureto maintain the temperature
  2. waitat 25° C. for 18 hours
  3. customthe THF is removed in vacuo,the residue
  4. extractionis extracted with ethyl acetate
  5. customthe extract is dried
  6. customevaporated
  7. customThe residual solid is recrystallized from isopropanol

出典と根拠

ORDレコード
ord-633593c12a7d4fa1bd1831ffcea2d9aa
出典データセット
uspto-grants-2001_04
特許番号
US06211234B1

関連ノート

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