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

HRID 1692956

Reaction equation

HRID 1692956 reaction equation
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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-d82995a021e0462dbcbc08fbd430253c
Source dataset
uspto-grants-2012_04
Patent number
US08158616B2

Linked notes

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