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

HRID 49347

Reaction equation

HRID 49347 reaction equation
[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]

Participants

10

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-bf97fe3a58d54acebbe41aec8f06c668
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Linked notes

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