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 485034노트

반응식

HRID 485034 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2f8184d7ebc54610ad76464104b2859b
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04535086

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