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Triphenylphosphine → Ethyl 3-{4-[2-(4-chlorophenyl)ethoxy]phenyl}-3-ethoxypropionate

HRID 1515080
ノート
印刷プレビュー

反応式

HRID 1515080 の反応式
[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:24]=[CH:23][C:22]([CH2:25][CH2:26]O)=[CH:21][CH:20]=1.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:24]=[CH:23][C:22]([CH2:25][CH2:26][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:21][CH:20]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 74647p-Chlorophenethylic alcoholHCID 66777355Diethylazodicarboxylate tolueneHCID 67058135Ethyl 3-ethoxy-3-(4-hydroxyphenyl)propionate

生成物 1

HCID 67058050Ethyl 3-{4-[2-(4-chlorophenyl)ethoxy]phenyl}-3-ethoxypropionate収率 95%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
50 °C

実験手順

Ethyl 3-ethoxy-3-(4-hydroxyphenyl)propionate (100 mg, 0.420 mmol) produced in Example 1 (1C) and 2-(4-chlorophenyl)ethanol (99 mg, 0.630 mmol) 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 yellow oily substance (151 mg, yield: 95%).

後処理

  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 yellow oily substance (151 mg, yield: 95%)

出典と根拠

ORDレコード
ord-cf0707538b08479086f077ff5d25f377
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08222281B2

反応ノート

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