Triphenylphosphine → Methyl 3-[4-[(3-anilinobenzyl)oxy]phenyl]propanoate

HRID 2422310

反応式

HRID 2422310 の反応式
[NH:1]([C:8]1[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=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>[NH:1]([C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[CH2:14][O:15][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 12882229(3-(Phenylamino)phenyl)methanolHCID 66777355Diethylazodicarboxylate toluene

生成物 1

HCID 57541953Methyl 3-[4-[(3-anilinobenzyl)oxy]phenyl]propanoate収率 50%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a mixture of (3-anilinophenyl)methanol (1.12 g, 5.62 mmol), methyl 3-(4-hydroxyphenyl)propanoate (1.22 g, 6.75 mmol), triphenylphosphine (1.92 g, 7.31 mmol) and tetrahydrofuran (20 mL) was added diethyl azodicarboxylate toluene solution (40%, 3.32 mL) with stirring at 0° C. and the mixture was stirred at room temperature for 14 hrs. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1) to give the title compound (1.01 g, yield 50%) as beige crystals.

後処理

  1. stirringthe mixture was stirred at room temperature for 14 hrs
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1)

出典と根拠

ORDレコード
ord-91d14e223e39464da398c116911a8c17
出典データセット
uspto-grants-2011_06
特許番号
US07960369B2

関連ノート

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