Sodium methanethiolate → HCID 86633661, compound

HRID 253522Notes

Reaction equation

HRID 253522 reaction equation
[CH3:1][C:2]([O:4][CH:5]([Cl:9])[CH:6]([CH3:8])[CH3:7])=O.C[S-:11].[Na+]>ClCCl.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][C:2]([O:4][CH:5]([Cl:9])[CH:6]([CH3:8])[CH3:7])=[S:11]

Participants

6

Reactant 2

HCID 4378561Sodium methanethiolateHCID 12661009HCID 12661009, compound

Product 1

HCID 86633661HCID 86633661, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1-chloro-2-methylpropyl methylformate in dichloromethane (DCM) was added a solution of sodium methanethiolate (CH3—SNa) (1.0 eq.) in water at 0° C. and 0.02 eq. of tetrabutylammonium bromide. The reactants were stirred at 0° C. for 30 min and then diluted with dichloromethane (DCM). The dichloromethane layer was allowed to separate, then washed with water and brine, and dried with anhydrous sodium sulfate (Na2SO4). After rotary evaporation to remove the solvent, the title compound (6a) was obtained. 1H-NMR (CDCl3): δ 1.05 (d, J=5.6 Hz, 3H), 1.07 (d, J=5.6 Hz, 3H), 2.18 (m, 1H), 2.38 (s, 3H), 6.34 (d, J=5.6 Hz, 1H) ppm.

Workup

  1. customto separate
  2. washwashed with water and brine
  3. dry with materialdried with anhydrous sodium sulfate (Na2SO4)
  4. customAfter rotary evaporation
  5. customto remove the solvent

Sources & evidence

ORD record
ord-524ac23436b4475b829b14ad4d818060
Source dataset
uspto-grants-2011_01
Patent number
US07872046B2

Reaction notes

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