Methyl iodide → 2-[5-(t-Butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]-1-methylpentyl]-1,4-difluorobenzene

HRID 748674Notes

Reaction equation

HRID 748674 reaction equation
[CH2:1]([Li])CCC.CCCCCC.[Si:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]([C:35]1[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=1[F:42])[S:25]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)(=[O:27])=[O:26])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].IC>O1CCCC1.O>[Si:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([C:35]1[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=1[F:42])([S:25]([C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1)(=[O:27])=[O:26])[CH3:1])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8058HexaneHCID 597507762-[5-(t-Butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]pentyl]-1,4-difluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 597507792-[5-(t-Butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]-1-methylpentyl]-1,4-difluorobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In an argon gas stream and at −78° C., n-butyl lithium (a 1.57M hexane solution, 0.294 ml, 0.461 mmol) was added to a solution of 2-[5-(t-butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]pentyl]-1,4-difluorobenzene (205 mg, 0.419 mmol) in tetrahydrofuran (4 ml). The mixture was stirred at room temperature for 1 hour. After cooling to −78° C., iodomethane (0.339 ml, 0.545 mmol) was added dropwise to the reaction mixture and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction mixture, followed by extraction with diethyl ether. The extracts were combined, washed successively with water and brine, dried over MgSO4, and then concentrated. The residue thus obtained was purified by medium-pressure chromatography on a silica gel column (6% ethyl acetate-hexane), whereby the title compound (168 mg, 80%) was obtained as a colorless oil.

Workup

  1. temperatureAfter cooling to −78° C.
  2. stirringthe mixture was stirred at room temperature for 4 hours
  3. extractionfollowed by extraction with diethyl ether
  4. washwashed successively with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue thus obtained
  8. customwas purified by medium-pressure chromatography on a silica gel column (6% ethyl acetate-hexane), whereby the title compound (168 mg, 80%)
  9. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-b659264b21f44a739cc726da2536de98
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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