Sodium Iodide → dimethyl 4-[5-((E)-1,5-diethyl-5-triethylsilanyloxyhept-1-enyl)-3-thienylmethoxy]phthalate

HRID 49347

반응식

HRID 49347 반응식
[CH2:1](/[C:3](/[C:20]1[S:24][CH:23]=[C:22]([CH2:25][OH:26])[CH:21]=1)=[CH:4]\[CH2:5][CH2:6][C:7]([CH2:18][CH3:19])([O:10][Si:11]([CH2:16][CH3:17])([CH2:14][CH3:15])[CH2:12][CH3:13])[CH2:8][CH3:9])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[Cl-].[NH4+].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].O[C:50]1[CH:51]=[C:52]([C:60]([O:62][CH3:63])=[O:61])[C:53](=[CH:58][CH:59]=1)[C:54]([O:56][CH3:57])=[O:55]>ClCCl.CC(=O)CC>[CH2:1](/[C:3](/[C:20]1[S:24][CH:23]=[C:22]([CH2:25][O:26][C:59]2[CH:58]=[C:53]([C:54]([O:56][CH3:57])=[O:55])[C:52](=[CH:51][CH:50]=2)[C:60]([O:62][CH3:63])=[O:61])[CH:21]=1)=[CH:4]\[CH2:5][CH2:6][C:7]([CH2:8][CH3:9])([O:10][Si:11]([CH2:16][CH3:17])([CH2:12][CH3:13])[CH2:14][CH3:15])[CH2:18][CH3:19])[CH3:2]

참가 물질

10

반응물 7

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 89726Dimethyl 4-hydroxyphthalateHCID 69825153[5-((E)-1,5-diethyl-5-triethylsilanyloxyhept-1-enyl)-3-thienyl]methanol

생성물 1

HCID 69929440dimethyl 4-[5-((E)-1,5-diethyl-5-triethylsilanyloxyhept-1-enyl)-3-thienylmethoxy]phthalate

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 6569Methyl Ethyl Ketone용매

반응 조건

온도
0 °C

실험 절차

3.9 g (9.8 mmol) of [5-((E)-1,5-diethyl-5-triethylsilanyloxyhept-1-enyl)-3-thienyl]methanol are dissolved in 100 mL of dichloromethane and the mixture is cooled to 0° C. 2 mL (15 mmol) of triethylamine are added, followed by 840 μL (10.7 mmol) of methanesulphonyl chloride. After stirring for 30 minutes, the medium is treated with ammonium chloride solution. The crude residue obtained is then dissolved in 100 mL of 2-butanone. 100 mg (0.7 mmol) of sodium iodide, 1.6 g (11.6 mmol) of potassium carbonate and 2 g (10 mmol) of dimethyl 4-hydroxyphthalate are added to this solution. The reaction medium is refluxed for 15 hours and then cooled and filtered through Celite. The residue obtained is purified by chromatography on a column of silica (eluent: 93 heptane/7 ethyl acetate). The desired product is obtained in the form of a colourless oil (m=1.7 g; Y=30%).

후처리

  1. customThe crude residue obtained
  2. temperatureThe reaction medium is refluxed for 15 hours
  3. temperaturecooled
  4. filtrationfiltered through Celite
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica (eluent: 93 heptane/7 ethyl acetate)

출처 및 근거

ORD 기록
ord-bf97fe3a58d54acebbe41aec8f06c668
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706725B1

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