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

HRID 322848

반응식

HRID 322848 반응식
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

참가 물질

6

반응물 4

HCID 962WaterHCID 18090802,4-Bis(benzyloxy)benzaldehydeHCID 17786294HCID 17786294, 화합물HCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-633593c12a7d4fa1bd1831ffcea2d9aa
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211234B1

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