Sodium methanethiolate → Ethyl 1-(methylthiomethyl)cyclopropanecarboxylate

HRID 1484759Notes

Reaction equation

HRID 1484759 reaction equation
[CH3:1][S-:2].[Na+].CS(O[CH2:9][C:10]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12][CH2:11]1)(=O)=O>CN(C)C=O.O>[CH3:1][S:2][CH2:9][C:10]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:12]1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 574666101-Methanesulfonyloxymethyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 66609952Ethyl 1-(methylthiomethyl)cyclopropanecarboxylateYield 100.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

Sodium methanethiolate (4.36 g, 62.30 mmol) was added to a stirred solution of ethyl 1-((methylsulfonyloxy)methyl)cyclopropanecarboxylate (6.92 g, 31.10 mmol) in N,N-dimethylformamide (62.30 mL) at 23° C. The resulting brown suspension was stirred at 23° C. for 18 h. The reaction mixture was diluted with water and extracted with diethyl ether. The combined organic layers were dried (MgSO4), filtered, and concentrated by rotary evaporation to afford the title compound as a brown oil (5.43 g, 100%): 1H NMR (300 MHz, CDCl3) δ 4.14 (q, J=7 Hz, 2H), 2.83 (s, 2H), 2.16 (s, 3H), 1.31 (dd, J=7, 4 Hz, 2H), 1.25 (t, J=7 Hz, 3H), 0.89 (dd, J=7, 4 Hz, 2H).

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-f5046d2a9f164a0cacb6e0fc023e4662
Source dataset
uspto-grants-2016_08
Patent number
US09422278B2

Reaction notes

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