Water → 1-Methoxy-4-methyl-2-(1-phenyl-vinyl)-benzene

HRID 393999

反応式

HRID 393999 の反応式
[CH2:1]1COCC1.C([Li])CCC.[CH3:11][O:12][C:13]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:14]=1[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O.O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:11][O:12][C:13]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:14]=1[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH2:1]

参加物

7

反応物 4

HCID 962WaterHCID 8028Tetrahydrofuran2 回HCID 249273(2-Methoxy-5-methylphenyl)(phenyl)methanoneHCID 178418339Butyllithium

生成物 1

HCID 113565331-Methoxy-4-methyl-2-(1-phenyl-vinyl)-benzene収率 83%

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 1140Toluene溶媒

反応条件

温度
-78 °C

実験手順

To a suspension of 7.58 g (21.2 mmole) methyltriphenylphosphoniumbromide in 15 ml abs. THF at room temperature within 10 minutes 17.0 ml (21.2) n-butyllithium (1.25M in n-hexane)are added dropwise. The reddish solution obtained is cooled to −78° C. and then within 15 minutes a solution of 3.70 g (16.3 mmole) 2-methoxy-5-methyl-benzophenone in 5 ml abs. THF is added. Agitation is performed initially for 20 minutes at −78° C. and for a further 8 h at room temperature. Then 80 ml water are added to the reaction mixture and extracted twice with 50 ml diethylether in each case. The purified organic phases are then dried through magnesium sulphate and the solvent is removed. Purification of the raw product obtained takes place by column chromatography on silica gel with toluene as the solvent. 3.03 g (13.5 mmole, 83%) 1-methoxy-4-methyl-2-(1-phenyl-vinyl)-benzene are obtained.

後処理

  1. customThe reddish solution obtained
  2. extractionextracted twice with 50 ml diethylether in each case
  3. dry with materialThe purified organic phases are then dried through magnesium sulphate
  4. customthe solvent is removed
  5. customPurification of the raw product
  6. customobtained

出典と根拠

ORDレコード
ord-2928a1ae3bd549cb9f1e9c91bee88482
出典データセット
uspto-grants-2004_10
特許番号
US06809225B2

関連ノート

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