Sodium methanethiolate → HCID 18701932, compound
Reaction equation
Cl[C:2]1[C:9]([CH2:10][CH2:11][CH3:12])=[C:8]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:21][S-:22].[Na+]>CN(C=O)C>[CH3:21][S:22][C:2]1[C:9]([CH2:10][CH2:11][CH3:12])=[C:8]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A solution of 2-chloro-3-propyl-4-benzyloxybenzaldehyde (Step C; 0.683 grams) in dry DMF (7 mL) was treated with sodium methanethiolate (0.166 grams). The solution was stirred at 50° C. for 3 hours. The reaction mixture was partitioned between isopropyl acetate and pH 7 buffer. The organic was washed 3 times with water, then dried over magnesium sulfate. Filtration and concentration afforded an oil which was chromatographed over silica gel to afford the title compound.