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

HRID 393999

반응식

HRID 393999 반응식
[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]

참가 물질

7

반응물 4

HCID 962WaterHCID 8028Tetrahydrofuran2회HCID 249273(2-Methoxy-5-methylphenyl)(phenyl)methanoneHCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 1140Toluene용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2928a1ae3bd549cb9f1e9c91bee88482
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809225B2

연결된 노트

불러오는 중…