Hexane → HCID 23028708, compound

HRID 748676

Reaction equation

HRID 748676 reaction equation
C([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].[Si:43]([O:50][CH2:51][CH2:52][CH2:53][CH2:54]I)([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44]>O.O1CCCC1>[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])([CH2:54][CH2:53][CH2:52][CH2:51][O:50][Si:43]([C:46]([CH3:47])([CH3:49])[CH3:48])([CH3:44])[CH3:45])[S:25]([C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1)(=[O:27])=[O:26])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 8058HexaneHCID 4250746tert-Butyl(4-iodobutoxy)dimethylsilaneHCID 59750776HCID 59750776, compoundHCID 178418339Butyllithium

Product 1

HCID 23028708HCID 23028708, compound

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, 0.358 ml, 0.562 mmol) was added to a tetrahydrofuran (4 ml) solution of the 2-[5-(t-butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]pentyl]-1,4-difluorobenzene (250 mg, 0.511 mmol) obtained in Example 15. The temperature of the resulting mixture was raised to room temperature. After cooling to −78° C., 4-(t-butyldimethylsilyloxy)-1-iodobutane (0.146 ml, 0.562 mmol) was added dropwise to the reaction mixture. The reaction mixture was stirred at room temperature for 3 days. 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 (167 mg, 48%) was obtained as a colorless solid.

Workup

  1. temperatureAfter cooling to −78° C.
  2. extractionfollowed by extraction with diethyl ether
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue thus obtained
  7. customwas purified by medium-pressure chromatography on a silica gel column (6% ethyl acetate-hexane), whereby the title compound (167 mg, 48%)
  8. customwas obtained as a colorless solid

Sources & evidence

ORD record
ord-d7cd4b9d3d83465c8cd14af07dfb58f8
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Linked notes

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