Tetrabutylammonium Fluoride → 6-(4-Chlorophenylsulfonyl)-6-(2-chloropyridin-3-yl)-1-hexanol

HRID 748720ノート

反応式

HRID 748720 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH:32]([C:43]1[C:44]([Cl:49])=[N:45][CH:46]=[CH:47][CH:48]=1)[S:33]([C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)(=[O:35])=[O:34])(C(C)(C)C)(C)C>O1CCCC1>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([S:33]([CH:32]([C:43]2[C:44]([Cl:49])=[N:45][CH:46]=[CH:47][CH:48]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][OH:26])(=[O:35])=[O:34])=[CH:37][CH:38]=1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 597508833-[6-(tert-Butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]hexyl]-2-chloropyridine

生成物 1

HCID 230288406-(4-Chlorophenylsulfonyl)-6-(2-chloropyridin-3-yl)-1-hexanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Under ice cooling, tetrabutylammonium fluoride (a 1 mol/l tetrahydrofuran solution; 0.70 ml) was added to a tetrahydrofuran (10 ml) solution of 3-[6-(tert-butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]hexyl]-2-chloropyridine (294 mg, 0.585 mmol). The resulting mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was washed successively with water and brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column. The fraction obtained from the hexane:ethyl acetate (=1:1) eluate was concentrated under reduced pressure, whereby the title compound (212 mg, 93%) was obtained as a colorless oil.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. washthe mixture was washed successively with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe fraction obtained from the hexane
  8. concentrationethyl acetate (=1:1) eluate was concentrated under reduced pressure, whereby the title compound (212 mg, 93%)
  9. customwas obtained as a colorless oil

出典と根拠

ORDレコード
ord-1e4e494417244254813c794458fb2123
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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