Methanol → Methyl 4-tetrahydrofuran-3-ylsulfonylbenzoate

Methyl 4-tetrahydrofuran-3-ylsulfanylbenzoate (1.01 g, 4.24 mmol) was dissolved in methanol (25 mL), followed by the addition of water (2.5 mL), and Oxone (2.61 g, 4.24 mmol). The reaction mixture was stirred at room temperature for 24 hours. An additional 0.1 eq of Oxone (0.26 g) was added and the reaction mixture was stirred for 2 hours, then filtered and the solvent was concentrated in vacuo. The resulting residue was dissolved in dichloromethane (30 mL) and washed with water (2×25 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to yield methyl 4-tetrahydrofuran-3-ylsulfonylbenzoate (1.07 g, 93%) as a yellow solid. ESI-MS m/z calc. 270.1. Found 271.3 (M+1)+; Retention time: 1.02 minutes (3 min run).

1. stirringthe reaction mixture was stirred for 2 hours
2. filtrationfiltered
3. concentrationthe solvent was concentrated in vacuo
4. dissolutionThe resulting residue was dissolved in dichloromethane (30 mL)
5. washwashed with water (2×25 mL)
6. dry with materialThe organic layer was dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-bd4edeaafe1e4006afa71032eb83d489

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08828996B2