Methyl iodide → Ethyl 7-(methylthio)chromane-2-carboxylate

HRID 39039Notes

Reaction equation

HRID 39039 reaction equation
[SH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1.CI.[C:19]([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:19][S:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66878558Ethyl 7-mercaptochromane-2-carboxylate

Product 1

HCID 66878197Ethyl 7-(methylthio)chromane-2-carboxylateYield 90.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of ethyl 7-mercaptochromane-2-carboxylate (3.4 g, 14.3 mmol), Methyliodide (3.03 g, 21.4 mmol) and K2CO3 (7.88 g, 57 mmol) in ACN (100 ml) was stirred for 2 h at RT. Filtration and evaporation of solvents gave the title compound (3.28 g). MS m/z (rel. intensity, 70 eV) 252 (M+, bp), 179 (94), 177 (40), 132 (55), 131 (63).

Workup

  1. filtrationFiltration and evaporation of solvents

Sources & evidence

ORD record
ord-1eeb636ac9a24272828b3c3b59ca6345
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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