Sodium methanethiolate → 2-Furanmethanethiol, 5-(3-pyridinyl)-

HRID 1913348Notes

Reaction equation

HRID 1913348 reaction equation
C(=O)([S:3][CH2:4][C:5]1[O:6][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1)C.C[S-].[Na+]>C(Cl)(Cl)Cl.CO>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:7]2[O:6][C:5]([CH2:4][SH:3])=[CH:9][CH:8]=2)[CH:11]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 11993872S-(5-(Pyridin-3-yl)furan-2-yl)methyl ethanethioate

Product 1

HCID 119938662-Furanmethanethiol, 5-(3-pyridinyl)-Yield 68%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

(See FIG. 7.) To a solution of 13 (10 mg, 0.05 mmol) in CHCl3/CH3OH (1.5 mL, 2:1, v:v) was added sodium thiomethoxide (3 mg, 0.05 mmol) and the resultant solution was stirred under argon for 10 min. The solvent was removed with a stream of argon and the residue was applied directly to a TLC plate (20×20 cm, 250 μm silica gel), developed (EtOAc/Hex, 5/95, Rf=0.12), the product band was scraped, extracted with dichloromethane and the solvent was removed in vacuo to afford the title compound 14 (6 mg, 68% yield) as a white film: 1H NMR (CD3OD) δ 8.72 (m, 1H), 8.19 (m, 1H), 7.96 (m, 1H), 7.28 (m, 1H), 6.66 (d, J=3.3 Hz, 1H), 6.07 (d, J=3.3 Hz, 1H), 3.59 (s, 2H), LRMS (ESI) m/z calcd for C10H10NOS [M+H]+ 192. found 192.

Workup

  1. customThe solvent was removed with a stream of argon
  2. extractionextracted with dichloromethane
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-19536217828f454fb49f4b788600f82c
Source dataset
uspto-grants-2013_12
Patent number
US08609708B2

Reaction notes

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