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

HRID 981477ノート

反応式

HRID 981477 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-13373c8e04cb4fada8a204b37e54929c
出典データセット
uspto-grants-1991_02
特許番号
US04992439

反応ノート

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