Triphenylphosphine → Ethyl 3-{4-[3-(3,4-dichlorophenyl)propoxy]phenyl}-3-ethoxypropionate

HRID 1515083

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HRID 1515083 반응식
[CH2:1]([O:3][CH:4]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[Cl:18][C:19]1[CH:20]=[C:21]([CH2:26][CH2:27][CH2:28]O)[CH:22]=[CH:23][C:24]=1[Cl:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:18][C:19]1[CH:20]=[C:21]([CH2:26][CH2:27][CH2:28][O:17][C:14]2[CH:13]=[CH:12][C:11]([CH:4]([O:3][CH2:1][CH3:2])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:16][CH:15]=2)[CH:22]=[CH:23][C:24]=1[Cl:25]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 190753133-(3,4-Dichlorophenyl)propan-1-ol2회HCID 66777355Diethylazodicarboxylate tolueneHCID 67058135Ethyl 3-ethoxy-3-(4-hydroxyphenyl)propionate

생성물 1

HCID 67058188Ethyl 3-{4-[3-(3,4-dichlorophenyl)propoxy]phenyl}-3-ethoxypropionate수율 73%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

Ethyl 3-ethoxy-3-(4-hydroxyphenyl)propionate (100 mg, 0.420 mmol) produced in Example 1 (1C) and 3-(3,4-dichlorophenyl)propanol (129 mg, 0.630 mmol) synthesized in (11A) were dissolved in tetrahydrofuran (10 mL), and triphenylphosphine (178 mg, 0.680 mmol) and a 40% diethyl azodicarboxylate toluene solution (309 μL, 0.680 mmol) were added thereto at room temperature, and then, the resulting mixture was stirred under a nitrogen atmosphere at 50° C. for 4 hours. After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 95:5 (v/v)), whereby the objective title compound was obtained as a colorless oily substance (130 mg, yield: 73%).

후처리

  1. temperatureAfter the reaction solution was cooled to room temperature
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 95:5 (v/v)), whereby the objective title compound
  4. customwas obtained as a colorless oily substance (130 mg, yield: 73%)

출처 및 근거

ORD 기록
ord-5d20314ba4d54297a24e199902750b6d
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222281B2

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