Hexane → HCID 59750887、化合物

HRID 748753ノート

反応式

HRID 748753 の反応式
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

参加物

8

反応物 4

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

生成物 1

HCID 59750887HCID 59750887、化合物収率 90.3%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-951c175a85c84c2ea921d20ebbaa3503
出典データセット
uspto-grants-2008_07
特許番号
US07399775B2

反応ノート

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