Methanol → 2-Methoxyethyl 3-(hydroxymethyl)-5-(pentafluoro-lambda6-sulphanyl)benzoate
Reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([S:14]([F:19])([F:18])([F:17])([F:16])[F:15])[CH:13]=1)[C:8]([OH:10])=[O:9].[CH3:20][O:21][CH2:22][CH2:23]Br.CO>CN(C=O)C>[OH:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([S:14]([F:19])([F:15])([F:16])([F:17])[F:18])[CH:13]=1)[C:8]([O:10][CH2:23][CH2:22][O:21][CH3:20])=[O:9]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
At 0° C., 86 mg (2.16 mmol) of sodium hydride (60% strength suspension in mineral oil) were added to a solution of 200 mg (0.719 mmol) of the compound of Example 37A in 5.7 ml of anhydrous DMF, and the mixture was then warmed to RT. 300 mg (2.16 mmol) of 2-bromoethyl methyl ether were then added, and the reaction mixture was stirred at 60° C. for about 16 h. After cooling to RT, 1 ml of methanol was added. In two portions, the reaction mixture was then separated into its components by preparative HPLC (Method 33). The product fractions were combined and concentrated on a rotary evaporator and the residue was dried under high vacuum. This gave 58 mg (20% of theory) of the title compound. In addition, 138 mg (57% of theory) of 2-methoxyethyl 3-(hydroxymethyl)-5-(pentafluoro-λ6-sulphanyl)benzoate were isolated, which were then reacted once more in the manner described above with 2-bromoethyl methyl ether to give a further 30 mg of the title compound.
Workup
- temperatureAfter cooling to RT
- customIn two portions, the reaction mixture was then separated into its components by preparative HPLC (Method 33)
- concentrationconcentrated on a rotary evaporator
- customthe residue was dried under high vacuum
Sources & evidence
- ORD record
- ord-f89e1accb3be4c8fbf5a3ac480624c54
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394309B2
Reaction notes
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