Hydrochloric Acid → 4-n-Propylbenzene t-butylsulfonamide

HRID 36110ノート

反応式

HRID 36110 の反応式
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:13])=[O:12])=[CH:6][CH:5]=1)[CH2:2][CH3:3].[Li]CCCC.B(OC(C)C)(OC(C)C)OC(C)C.Cl>C1COCC1>[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:2][CH3:3].[C:14]([S:11]([NH2:10])(=[O:13])=[O:12])([CH3:17])([CH3:16])[CH3:15]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 194258794-n-Propylphenyl-t-butylsulfonamideHCID 178418339Butyllithium

生成物 1

HCID 194258774-n-Propylbenzene t-butylsulfonamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-n-propylphenyl-t-butylsulfonamide (2.85 g, 11.2 mmoL) in anhydrous THF (20 mL) cooled to -40° C. under N2 was added 2.5M n-BuLi solution (11.2 mL, 2.5 equiv). The mixture was warmed to rt and stirred for 2 h. To the mixture, containing the bright red dianion at 0° C., was added B(OiPr)3 (3.9 mL, 1.5 equiv). The next day 2N HCl (3 mL) was added and the mixture was stirred for 1 h. The solvent was removed under reduced pressure and the residue was extracted with EtOAc. The organic was washed with 2N HCl, H2O and brine. The organic was dried over anhydrous MgSO4 and concentrated in vacuo to afford the titled compound. Rf=0.5 (1:1 EtOAc/Hex). The crude material was used in subsequent steps without further purification.

後処理

  1. additionTo the mixture, containing the bright red dianion at 0° C.
  2. stirringthe mixture was stirred for 1 h
  3. customThe solvent was removed under reduced pressure
  4. extractionthe residue was extracted with EtOAc
  5. washThe organic was washed with 2N HCl, H2O and brine
  6. dry with materialThe organic was dried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-c499ed1d523643029c3e0d4e817a16f2
出典データセット
uspto-grants-1995_05
特許番号
US05412097

反応ノート

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