Dimethylformamide → 5-((E)-1,5-diethyl-5-triethylsilanyloxyhept-1-enyl)thiophene-3-carbaldehyde

HRID 49345노트

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HRID 49345 반응식
Br[C:2]1[CH:3]=[C:4](/[C:7](/[CH2:24][CH3:25])=[CH:8]/[CH2:9][CH2:10][C:11]([CH2:22][CH3:23])([CH2:20][CH3:21])[O:12][Si:13]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:14][CH3:15])[S:5][CH:6]=1.C([Li])CCC.CN(C)[CH:33]=[O:34].[Cl-].[NH4+]>C1COCC1>[CH2:24](/[C:7](/[C:4]1[S:5][CH:6]=[C:2]([CH:33]=[O:34])[CH:3]=1)=[CH:8]\[CH2:9][CH2:10][C:11]([CH2:22][CH3:23])([O:12][Si:13]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:14][CH3:15])[CH2:20][CH3:21])[CH3:25]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 69825241[(e)-5-(4-Bromo-2-thienyl)-1,1-diethylhept-4-enyloxy]triethylsilaneHCID 178418339Butyllithium

생성물 1

HCID 867593895-((E)-1,5-diethyl-5-triethylsilanyloxyhept-1-enyl)thiophene-3-carbaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

11 g (24.7 mmol) of [(E)-5-(4-bromo-2-thienyl)-1,1-diethylhept-4-enyloxy]triethylsilane are dissolved in 100 mL of anhydrous THF and the mixture is cooled to −78° C. 10.9 mL (27 mmol) of 2.5 M butyllithium are added slowly and the mixture is stirred for 15 minutes. 2.1 mL (27 mmol) of dimethylformamide are then added and the medium is stirred for 30 minutes and then poured into aqueous ammonium chloride solution. After extraction with ethyl acetate and chromatography on silica gel (eluent: 9 heptane/1 ethyl acetate), the product is obtained in the form of a colourless oil (m=4 g; Y=41%).

후처리

  1. stirringthe medium is stirred for 30 minutes
  2. extractionAfter extraction with ethyl acetate and chromatography on silica gel (eluent: 9 heptane/1 ethyl acetate)
  3. customthe product is obtained in the form of a colourless oil (m=4 g; Y=41%)

출처 및 근거

ORD 기록
ord-6dbcfd73dfe4425bbfccfb8343299adb
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706725B1

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