Ethyl Acetate → 2-[3-[2-(t-Butyldiphenylsilyloxy)ethylthio]-1-[(4-chlorophenyl)sulfonyl]propyl]-1,4-difluorobenzene

HRID 748793

反応式

HRID 748793 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Si:20]([O:37][CH2:38][CH2:39][S:40][CH2:41][CH2:42]O)([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(C=P(CCCC)(CCCC)CCCC)#N.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Si:20]([O:37][CH2:38][CH2:39][S:40][CH2:41][CH2:42][CH:11]([C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[F:19])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])([C:33]([CH3:35])([CH3:36])[CH3:34])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 4622928Cyanomethylenetributylphosphorane2 回HCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzeneHCID 597508072-[2-(t-Butyldiphenylsilyloxy)ethylthio]ethanol2 回

生成物 1

HCID 590282472-[3-[2-(t-Butyldiphenylsilyloxy)ethylthio]-1-[(4-chlorophenyl)sulfonyl]propyl]-1,4-difluorobenzene収率 95%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

The 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (900 mg, 2.97 mmol) obtained in Example 5 and 2-[2-(t-butyldiphenylsilyloxy)ethylthio]ethanol (1.64 g, 4.55 mmol) were dissolved in toluene (20 ml), followed by the addition of cyanomethylenetri-n-butylphosphorane (1.26 g, 5.22 mmol). Under an argon atmosphere, the resulting mixture was heated under reflux for 9 hours. After the reaction mixture was allowed to cool down, 2-[2-(t-butyldiphenylsilyloxy)ethylthio]ethanol (500 mg, 1.39 mmol) and cyanomethylenetri-n-butylphosphorane (400 mg, 1.66 mmol) were added thereto. Under an argon atmosphere, the mixture was heated under reflux for 14 hours. After the reaction mixture was allowed to cool down, it was concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=10:1 eluate was concentrated under reduced pressure, whereby the title compound (1.82 g, 2.82 mmol, 95%) was obtained as a pale yellowish brown oil.

後処理

  1. temperatureUnder an argon atmosphere, the resulting mixture was heated
  2. temperatureunder reflux for 9 hours
  3. temperatureto cool down
  4. temperatureUnder an argon atmosphere, the mixture was heated
  5. temperatureunder reflux for 14 hours
  6. temperatureto cool down
  7. concentrationit was concentrated under reduced pressure
  8. customthe fraction obtained from the hexane

出典と根拠

ORDレコード
ord-0feb3f71d7a24672bd61820c292fa44d
出典データセット
uspto-grants-2008_07
特許番号
US07399775B2

関連ノート

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