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

HRID 1966170

반응식

HRID 1966170 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-cef10a2d79b84909a97b64b11bcc95c9
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420629B2

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