Hexane → HCID 59750887, 화합물

HRID 748753노트

반응식

HRID 748753 반응식
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[F:9].CCCCCC.C([Li])CCC.[Si:21]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH:45]=[O:46])([C:34]([CH3:37])([CH3:36])[CH3:35])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCC)(=O)C.C(OCC)C.O1CCCC1>[Si:21]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH:45]([C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[F:9])[OH:46])([C:34]([CH3:36])([CH3:37])[CH3:35])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

참가 물질

8

반응물 4

HCID 8058HexaneHCID 678622-Bromo-1,4-difluorobenzeneHCID 108831267-(t-butyldiphenylsilyloxy)heptanalHCID 178418339Butyllithium

생성물 1

HCID 59750887HCID 59750887, 화합물수율 90.3%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

A tetrahydrofuran (40 ml) solution of 1-bromo-2,5-difluorobenzene (1.21 ml, 10.7 mmol) was stirred at −78° C., followed by the addition of a hexane solution (8.50 ml, 13.4 mmol) of n-butyl lithium. The reaction mixture was added to a tetrahydrofuran (20 ml) solution of 7-(t-butyldiphenylsilyloxy)heptanal (3.28 g, 8.90 mmol) at −78° C. and the mixture was stirred at the same temperature for 30 minutes. After the temperature of the reaction mixture was elevated to room temperature, diethyl ether was added thereto. The mixture was washed with a saturated aqueous solution of ammonium chloride. The organic layer was then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=9:1 eluate was concentrated under reduced pressure, whereby the title compound (3.88 g, 8.04 mmol, 90%) was obtained as a colorless oil.

후처리

  1. customwas elevated to room temperature
  2. washThe mixture was washed with a saturated aqueous solution of ammonium chloride
  3. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe fraction obtained from the hexane

출처 및 근거

ORD 기록
ord-951c175a85c84c2ea921d20ebbaa3503
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399775B2

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