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

HRID 748678Notes

Reaction equation

HRID 748678 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[Si:6]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([C:29]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=1[F:36])[S:19]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)(=[O:21])=[O:20])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].CN(C)P(=O)(N(C)C)N(C)C.ICCCC>C(O)(C)C.O1CCCC1.CCCCCC>[Si:6]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([C:29]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=1[F:36])([S:19]([C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=1)(=[O:21])=[O:20])[CH2:1][CH2:2][CH2:3][CH3:4])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

8

Reactant 4

HCID 10962Butyl iodideHCID 12679HexamethylphosphoramideHCID 597507762-[5-(t-Butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]pentyl]-1,4-difluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 597507422-[5-(t-Butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]-1-butylpentyl]-1,4-difluorobenzene

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

In an argon gas stream and at −78° C., n-butyl lithium (a 1.57M hexane solution, 0.287 ml, 0.450 mmol) was added to a tetrahydrofuran (4 ml) solution of the 2-[5-(t-butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]pentyl]-1,4-difluorobenzene (200 mg, 0.409 mmol) obtained in Example 15. The temperature of the resulting mixture was raised to room temperature. After cooling to −78° C., hexamethylphosphoric triamide (0.214 ml, 1.23 mmol) and iodobutane (51.1 μl, 0.450 mmol) were added dropwise to the reaction mixture. The resulting mixture was stirred at room temperature for 20 hours. Isopropanol (0.5 ml) was added to the reaction mixture, followed by concentration. The residue thus obtained was purified by medium-pressure chromatography on a silica gel column (5% ethyl acetate-hexane), whereby the title compound (163 mg, 73%) was obtained as a colorless oil.

Workup

  1. temperatureAfter cooling to −78° C.
  2. concentrationfollowed by concentration
  3. customThe residue thus obtained
  4. customwas purified by medium-pressure chromatography on a silica gel column (5% ethyl acetate-hexane), whereby the title compound (163 mg, 73%)
  5. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-c7bc6e5a06b045b795baa43bd0e35a8c
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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