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

HRID 49347

反応式

HRID 49347 の反応式
[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]

参加物

10

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 6569Methyl Ethyl Ketone溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-bf97fe3a58d54acebbe41aec8f06c668
出典データセット
uspto-grants-2004_03
特許番号
US06706725B1

関連ノート

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