Hexane → HCID 59750776, 화합물

HRID 748673

반응식

HRID 748673 반응식
C([Li])CCC.CCCCCC.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH2:22][C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[F:30])(=[O:21])=[O:20])=[CH:15][CH:14]=1.[Si:31]([O:38][CH2:39][CH2:40][CH2:41][CH2:42]I)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>O.C(COC)OC>[Si:31]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH:22]([C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[F:30])[S:19]([C:16]1[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=1)(=[O:21])=[O:20])([C:34]([CH3:35])([CH3:36])[CH3:37])([CH3:32])[CH3:33]

참가 물질

7

반응물 4

HCID 8058HexaneHCID 4250746tert-Butyl(4-iodobutoxy)dimethylsilaneHCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzeneHCID 178418339Butyllithium

생성물 1

HCID 59750776HCID 59750776, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
-78 °C

실험 절차

In an argon gas stream and at −78° C., n-butyl lithium (a 1.57M hexane solution, 0.701 ml, 1.10 mmol) was added to a dimethoxyethane (5 ml) solution of the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (303 mg, 1.00 mmol) obtained in Example 5. The mixture was stirred at −78° C. for 1 hour and then, at room temperature for 30 minutes. The reaction mixture was cooled to −78° C., followed by the dropwise addition of 4-(t-butyldimethylsilyloxy)-1-iodobutane (0.260 ml, 1.00 mmol). While elevating the temperature of the reaction mixture to room temperature, stirring was conducted for 15 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 concentrated. The residue thus obtained was purified by medium-pressure chromatography on a silica gel column (8% ethyl acetate-hexane), whereby the title compound (401 mg, 82%) was obtained as a colorless solid. The resulting solid was recrystallized from hexane to yield colorless needle crystals.

후처리

  1. waitat room temperature for 30 minutes
  2. temperatureThe reaction mixture was cooled to −78° C.
  3. customto room temperature
  4. stirringstirring
  5. waitwas conducted for 15 hours
  6. extractionfollowed by extraction with diethyl ether
  7. washwashed successively with water and brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe residue thus obtained
  11. customwas purified by medium-pressure chromatography on a silica gel column (8% ethyl acetate-hexane), whereby the title compound (401 mg, 82%)
  12. customwas obtained as a colorless solid
  13. customThe resulting solid was recrystallized from hexane
  14. customto yield colorless needle crystals

출처 및 근거

ORD 기록
ord-bce6c0c610834911a1353b39d816ba56
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399775B2

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