Triphenylphosphine → Methyl [3-[2-(1,6-dihydro-6-oxo-3,4-diphenyl-1-pyridazinyl)ethyl]phenoxyacetate]

HRID 981477노트

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HRID 981477 반응식
N(C(OCC)=O)=NC(OCC)=O.[C:13]1([C:19]2[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:23][NH:22][C:21](=[O:31])[CH:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O[CH2:33][CH2:34][C:35]1[CH:36]=[C:37]([CH:44]=[CH:45][CH:46]=1)[O:38][CH2:39][C:40]([O:42][CH3:43])=[O:41].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[O:31]=[C:21]1[N:22]([CH2:33][CH2:34][C:35]2[CH:36]=[C:37]([CH:44]=[CH:45][CH:46]=2)[O:38][CH2:39][C:40]([O:42][CH3:43])=[O:41])[N:23]=[C:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:20]1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 1509765,6-Diphenyl-3(2H)-pyridazinoneHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10013334Acetic acid, [3-(2-hydroxyethyl)phenoxy]-, methyl ester

생성물 1

HCID 15734802Methyl [3-[2-(1,6-dihydro-6-oxo-3,4-diphenyl-1-pyridazinyl)ethyl]phenoxyacetate]수율 98%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Diethyl azodicarboxylate (2.73 g, 2.50 mL, 16 mmol) was added to a stirred solution of 5,6-diphenyl-3(2H)-pyridazinone (3.00 g, 12 mmol), methyl [3-(2-hydroxyethyl)-phenoxy]acetate (2.80 g, 13 mmol) and triphenylphosphine (4.12 g, 16 mmol) in dry THF (75 mL) maintained at 0° C. The ice bath was removed and the mixture stirred at room temperature for 1.75 hours before removal of the solvent. The residue was chromatographed twice on columns of silica gel using mixtures of diethyl ether and hexanes (7:3) and then (3:2) as eluent to give methyl [3-[2-(1,6-dihydro-6-oxo-3,4-diphenyl-1-pyridazinyl)ethyl]phenoxyacetate] (5.12 g, 98%), contaminated with 0.6 equivalents of 1,2-dicarbethoxy hydrazine, as a white foam.

후처리

  1. customThe ice bath was removed
  2. customThe residue was chromatographed twice on columns of silica gel using mixtures of diethyl ether and hexanes (7:3)

출처 및 근거

ORD 기록
ord-13373c8e04cb4fada8a204b37e54929c
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04992439

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