Triphenylphosphine → 4-(3,4-Dichlorobenzyloxy)-2-methoxybenzaldehyde

HRID 1515100노트

반응식

HRID 1515100 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:16]O.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:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:16][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 157283,4-Dichlorobenzyl alcoholHCID 5195414-Hydroxy-2-MethoxybenzaldehydeHCID 66777355Diethylazodicarboxylate toluene

생성물 1

HCID 772313794-(3,4-Dichlorobenzyloxy)-2-methoxybenzaldehyde수율 96.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-Hydroxy-2-methoxybenzaldehyde (408 mg, 2.68 mmol), 3,4-dichlorobenzyl alcohol (665 mg, 3.76 mmol), and triphenylphosphine (980 mg, 3.74 mmol) were dissolved in tetrahydrofuran (8 mL), and a diethyl azodicarboxylate toluene solution (2.2 M, 1.71 mL, 3.76 mmol) was slowly added dropwise thereto at room temperature, and then, the resulting mixture was stirred under a nitrogen atmosphere at room temperature for 2 hours. The solvent in the reaction solution was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 90:10 (v/v)), whereby the objective title compound was obtained as a white solid (801 mg, yield: 96%).

후처리

  1. distillationThe solvent in the reaction solution was distilled off under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 90:10 (v/v)), whereby the objective title compound

출처 및 근거

ORD 기록
ord-6db5d53681db4b2db030822ec8022df2
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222281B2

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