Dimethyl Sulfide → HCID 21848322, compound
Reaction equation
[O:1]=[O+][O-].[F:4][C:5]1[CH:14]=[CH:13][C:8]2[CH:9]=C(C)[O:11][C:7]=2[C:6]=1[CH2:15][CH2:16][CH3:17].CSC>>[F:4][C:5]1[CH:14]=[CH:13][C:8]([CH:9]=[O:1])=[C:7]([OH:11])[C:6]=1[CH2:15][CH2:16][CH3:17]Participants
Procedure
Ozone was conducted at -78° into a solution of 4.8 g (25 mmol) of 6-fluoro-2-methyl-7-propyl-benzofuran until the colour became blue. Subsequently, argon was conducted through the solution which was then treated at -78° with 10 ml (136 mmol) of dimethyl sulfide. After warming to room temperature the solution was concentrated in a vacuum and the residue was dissolved in 40 ml of ethanol. After the addition of 20 ml of 3% sodium hydrogen carbonate solution the mixture was stirred at 70° for 30 minutes. Subsequently, the mixture was poured on to 200 ml of ice-water, made acid with 10% HCl and extracted three times with 150 ml of diethyl ether each time. After drying over sodium sulfate concentration was carried out in a vacuum. The crude product obtained was purified by column chromatography on silica gel (dichloromethane). There were obtained 3.3 g (72%) of 4-fluoro-2-hydroxy-3-propyl-benzaldehyde as a pale yellow oil.
Workup
- concentrationwas concentrated in a vacuum
- dissolutionthe residue was dissolved in 40 ml of ethanol
- additionAfter the addition of 20 ml of 3% sodium hydrogen carbonate solution the mixture
- additionSubsequently, the mixture was poured on to 200 ml of ice-water
- extractionextracted three times with 150 ml of diethyl ether each time
- dry with materialAfter drying over sodium sulfate concentration
- customThe crude product obtained
- customwas purified by column chromatography on silica gel (dichloromethane)
Sources & evidence
- ORD record
- ord-fb13efa2075a4847a88f1a45a5d6137e
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05955495
Reaction notes
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