Methanol--water (1/1) → Ethyl 3-methyl-7-(4,5,6,7-tetrahydro-4,4,7,7-tetramethylbenzo[b]thien-2-yl)-2,4,6-octatrienoate

HRID 542903ノート

反応式

HRID 542903 の反応式
[Br-].[CH3:2][C:3]1([CH3:35])[C:11]2[CH:10]=[C:9]([CH:12]([P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH3:13])[S:8][C:7]=2[C:6]([CH3:34])([CH3:33])[CH2:5][CH2:4]1.[CH:36]([CH:38]=[CH:39][C:40]([CH3:47])=[CH:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])=O.CO.O>C1OCCC1>[CH3:47][C:40]([CH:39]=[CH:38][CH:36]=[C:12]([C:9]1[S:8][C:7]2[C:6]([CH3:33])([CH3:34])[CH2:5][CH2:4][C:3]([CH3:2])([CH3:35])[C:11]=2[CH:10]=1)[CH3:13])=[CH:41][C:42]([O:44][CH2:45][CH3:46])=[O:43]

参加物

5

反応物 3

HCID 22242641Methanol--water (1/1)HCID 23049224[1-(4,5,6,7-Tetrahydro-4,4,7,7-tetramethylbenzo-[b]thien-2-yl)ethyl]triphenylphosphonium bromideHCID 54439227Ethyl 5-formyl-3-methyl-2,4-pentadienoate

生成物 1

HCID 53882835Ethyl 3-methyl-7-(4,5,6,7-tetrahydro-4,4,7,7-tetramethylbenzo[b]thien-2-yl)-2,4,6-octatrienoate収率 83.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4.50 g of [1-(4,5,6,7-tetrahydro-4,4,7,7-tetramethylbenzo[b]thien-2-yl)ethyl]triphenylphosphonium bromide and 1.3 g of ethyl 5-formyl-3-methylpenta-2,4-dienoate are dissolved in 70 ml of butylene oxide and the solution is heated at reflux for 2 hours. The cooled mixture is poured into a methanol/water mixture (6:4) and extracted several times with hexane. The hexane phase is washed three times with water, dried and evaporated. After filtration of the crude product over silica gel (eluting agent hexane/ether 9:1), there are obtained 2.4 g of ethyl 3-methyl-7-(4,5,6,7-tetrahydro-4,4,7,7-tetramethylbenzo[b]thien-2-yl)-2,4,6,-octatrienoate as a pale yellowish oil.

後処理

  1. temperaturethe solution is heated
  2. temperatureat reflux for 2 hours
  3. extractionextracted several times with hexane
  4. washThe hexane phase is washed three times with water
  5. customdried
  6. customevaporated
  7. filtrationAfter filtration of the crude product over silica gel (eluting agent hexane/ether 9:1), there

出典と根拠

ORDレコード
ord-3a698e2121af45f3a1fb5a518e8e9a07
出典データセット
uspto-grants-1987_04
特許番号
US04659735

反応ノート

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