Hexane → 1-Bromo-4-[4-(methoxymethylidene)cyclohexyl]benzene

HRID 1975614ノート

反応式

HRID 1975614 の反応式
[Cl-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][O:10][CH3:11])C=CC=CC=1.[Br:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]2[CH2:36][CH2:35][C:34](=O)[CH2:33][CH2:32]2)=[CH:27][CH:26]=1.CCCCCC>COC(C)(C)C.O1CCCC1>[Br:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]2[CH2:36][CH2:35][C:34](=[CH:9][O:10][CH3:11])[CH2:33][CH2:32]2)=[CH:27][CH:26]=1

参加物

6

反応物 3

HCID 8058HexaneHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 100835924-(4-Bromophenyl)cyclohexanone

生成物 1

HCID 190979141-Bromo-4-[4-(methoxymethylidene)cyclohexyl]benzene収率 93.6%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 15413tert-Butyl methyl ether溶媒

実験手順

20.4 g of triphenyl-methoxymethyl-phosphonium chloride were suspended in 60 ml of t-butyl methyl ether while gassing with argon in a sulphonation flask having a thermometer, mechanical stirrer, dropping funnel and solid substance addition tube and treated at -10° C. within 10 minutes with 6.6 g of solid potassium t-butylate. After completion of the addition the mixture was stirred at -10° C. to 0° C. for 30 minutes, then the deep orange, heterogeneous reaction mixture was treated dropwise at 0° C. with a solution of 10 g of 4-(4-bromophenyl)cyclohexanone in 50 ml of absolute tetrahydrofuran, subsequently stirred at room temperature for 24 hours, poured into 500 ml of hexane and filtered. Low-pressure chromatography of the concentrated residue (13.9 g) on silica gel with hexane/ethyl acetate (vol. 9:1) gave 10.4 g of 1-bromo-4-[4-(methoxymethylidene)cyclohexyl]benzene as a colourless oil.

後処理

  1. customwhile gassing with argon in a sulphonation flask
  2. additionfunnel and solid substance addition tube
  3. additionAfter completion of the addition the mixture
  4. stirringsubsequently stirred at room temperature for 24 hours
  5. filtrationfiltered

出典と根拠

ORDレコード
ord-c7d89244b33a41298f701f20d983df87
出典データセット
uspto-grants-1994_02
特許番号
US05288428

反応ノート

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