Hexane → HCID 23028708, 화합물

HRID 748676

반응식

HRID 748676 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 23028708HCID 23028708, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d7cd4b9d3d83465c8cd14af07dfb58f8
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399775B2

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