Ethanol → 2-{[(2-Methylfuran-3-yl)sulfanyl]methyl}pyridine
Reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[SH:7].C(O)C.Cl.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18]Cl.C[O-].[Na+]>CO.C(O)(C)C>[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[S:7][CH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=1Participants
Procedure
The 3-furyl sulfides of our invention can also be prepared by reacting 3-furan thiols, e.g. 2-methyl-3-furan thiol with an appropriate aralkyl halide or nitrogen heterocyclic halide, or alkenyl halide or alkylthiolalkyl halide (e.g. bromide or chloride); (i) in the presence of a base such as an alkali metal alkoxide (e.g., sodium methoxide); (ii) at a temperature in the range of 15°-65° C; and (iii) in a suitable solvent, e.g., an anhydrous lower alkanol such as anhydrous methanol, ethanol or isopropanol. Thus, for example, alpha picolyl chloride hydrochloride, when reacted with 2-methyl-3-furan thiol in anhydrous methanol in the presence of sodium methoxide at a temperature of 24° C will yield (2-methyl-3-furyl)(2-pyridylmethyl) sulfide. Thus, as a further example, in a methanol solvent sodium methylate is reacted with 2-methyl-3-furan thiol to form the corresponding mercaptide which is, in turn, reacted with allyl bromide at reflux temperature and 1 atmosphere pressure thereby forming (allyl)(2-methyl-3-furyl) sulfide.
Workup
- customin the range of 15°-65° C
Sources & evidence
- ORD record
- ord-28b2edf977894f8bb78602d91ff098e3
- Source dataset
- uspto-grants-1976_10
- Patent number
- US03988510
Reaction notes
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