Dimethyl Sulfide → HCID 53660136, compound

HRID 1741979Notes

Reaction equation

HRID 1741979 reaction equation
[Cl:1]N1C(=O)CCC1=O.CSC.[Si:12]([O:29][CH2:30][CH2:31][CH2:32][O:33][CH:34]1[CH:39]([O:40][Si:41]([C:54]([CH3:57])([CH3:56])[CH3:55])([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:38][C:37](=[C:58](O)[CH3:59])[C:36](=[CH2:61])[CH:35]1[O:62][Si:63]([C:76]([CH3:79])([CH3:78])[CH3:77])([C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[Na+]>C(Cl)Cl.C(OCC)C>[Si:12]([O:29][CH2:30][CH2:31][CH2:32][O:33][CH:34]1[CH:39]([O:40][Si:41]([C:54]([CH3:57])([CH3:56])[CH3:55])([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:38][C:37](=[CH:58][CH2:59][Cl:1])[C:36](=[CH2:61])[CH:35]1[O:62][Si:63]([C:76]([CH3:79])([CH3:78])[CH3:77])([C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 1068Dimethyl SulfideHCID 5234Sodium ChlorideHCID 31398ChlorosuccinimideHCID 131718634HCID 131718634, compound

Product 1

HCID 53660136HCID 53660136, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-25 °C

Procedure

N-chlorosuccinimide (140 mg) was suspended in 10 ml of methylene chloride, and 74 mg of dimethyl sulfide was added at 0° C. The mixture was stirred, and cooled to -25° C. A solution of 958 mg of (4-(3-tert-butyldiphenylsilyloxypropoxy)-3,5-bis-(tert -butyldiphenylsilyloxy)-2-methylenecyclohexylidene) ethanol in 2 ml of methylene chloride was added dropwise, followed by stirring at 0° C. for 2 hours. A sodium chloride aqueous solution was added to the reaction mixture, and extraction was conducted with diethyl ether. The extract was washed with a sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. There resulted 931 mg of (4-(3-tert-butyldiphenylsilyloxypropoxy)-3,5-bis-(tert-butyldiphenylsilyloxy)-2-methylenecyclohexylidene)ethyl chloride.

Workup

  1. stirringby stirring at 0° C. for 2 hours
  2. washThe extract was washed with a sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-90de5341a4d6400195f23aa580ef857a
Source dataset
uspto-grants-1994_08
Patent number
US05334740

Reaction notes

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