Sodium methanethiolate → 2-(4-Hydroxy-phenyl)-7-methylsulfanylmethyl-benzofuran-5-ol
Reaction equation
Br[CH2:2][C:3]1[C:11]2[O:10][C:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)=[CH:8][C:7]=2[CH:6]=[C:5]([OH:19])[CH:4]=1.[CH3:20][S-:21].[Na+]>CO>[OH:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[O:10][C:11]3[C:3]([CH2:2][S:21][CH3:20])=[CH:4][C:5]([OH:19])=[CH:6][C:7]=3[CH:8]=2)=[CH:13][CH:14]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of benzyl bromide 4 (0.052 g, 0.161 mmole) in 5 mL methanol was added sodium thiomethoxide (0.013 g, 0.177 mmole). After stirring at R.T. for 1 hour, the solvent was evaporated and the residue was poured into water and extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate, water, brine, and dried with magnesium sulfate. The organic phases were concentrated and the residue was loaded on to silica gel and chromatographed with silica gel (hexanes:ethyl acetate, 4:1) to afford 0.025 g (54%) of thioether 10 as a white solid: Mp=188–190° C.; 1H NMR (DMSO-d6) δ 9.82 (s, 1 H), 9.14 (s, 1 H), 7.69 (d, 2 H, J=8.5 Hz), 7.01 (s, 1 H), 6.86 (d, 2 H, J=8.5 Hz), 6.77 (d, 1H, J=2.1 Hz), 6.63 (d, 1 H, J=2.1 Hz), 3.91 (s, 2 H), 2.05 (s, 3 H); MS 285 (M−H)−
Workup
- customthe solvent was evaporated
- additionthe residue was poured into water
- extractionextracted with ethyl acetate
- washThe combined organic phases were washed with saturated sodium bicarbonate, water, brine
- dry with materialdried with magnesium sulfate
- concentrationThe organic phases were concentrated
- customchromatographed with silica gel (hexanes:ethyl acetate, 4:1)
Sources & evidence
- ORD record
- ord-d7fa017282484c018ae438b66628b4e0
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07022733B2
Reaction notes
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