Methyl (methylsulfinyl)methyl sulfide → [[[3-(methylsulfinyl)-3-(methylthio)cyclobutyl]oxy]methyl]Benzene

HRID 1966170

反応式

HRID 1966170 の反応式
C([Li])CCC.[CH3:6][S:7]([CH2:9][S:10][CH3:11])=[O:8].Br[CH2:13][CH:14]([CH2:23]Br)[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCCCCC.C1COCC1.ClCCl>[CH3:6][S:7]([C:9]1([S:10][CH3:11])[CH2:13][CH:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:23]1)=[O:8]

参加物

7

反応物 3

HCID 99129Methyl (methylsulfinyl)methyl sulfideHCID 561824(((1,3-Dibromopropan-2-yl)oxy)methyl)benzeneHCID 178418339Butyllithium

生成物 1

HCID 13298802[[[3-(methylsulfinyl)-3-(methylthio)cyclobutyl]oxy]methyl]Benzene収率 56%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

2.5 M of n-butyllithium in hexane (19 mL) was added to a solution of (methylsulfinyl)(methylthio)methane (5.0 g, 0.040 mol) in THF (10 mL) dropwise at −10° C. and the mixture was stirred for 3 h. To the resultant solution was added dropwise [2-bromo-1-(bromomethyl)ethoxy]methylbenzene (4.9 g, 0.016 mol) at −70° C. over 30 min. The mixture was stirred at this temperature for 3 h and then at rt over night. The reaction was diluted with dichloromethane and washed with water. The aqueous phases were extracted with dichloromethane. The organic layers were combined, washed with brine, dried over MgSO4, concentrated and purified with Combiflash (silica gel, 0-55% EtOAc/Hex) to give the desired product (2.4 g, 56%) as brown oil. LCMS (M+Na) 293.3. 1H NMR (400 MHz, CDCl3): δ 7.30 (5H, m), 4.45 (2H, s), 4.33 (1H, m), 2.75 (2H, m), 2.65 (2H, m), 2.41 (3H, s), 2.12 (3H, s) ppm.

後処理

  1. stirringThe mixture was stirred at this temperature for 3 h
  2. waitat rt over night
  3. washwashed with water
  4. extractionThe aqueous phases were extracted with dichloromethane
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. custompurified with Combiflash (silica gel, 0-55% EtOAc/Hex)

出典と根拠

ORDレコード
ord-cef10a2d79b84909a97b64b11bcc95c9
出典データセット
uspto-grants-2013_04
特許番号
US08420629B2

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