1,1-Dioxo-1lambda6-thiolane-3-carboxylic acid → 3-(Hydroxymethyl)-1lambda6-thiolane-1,1-dione
Reaction equation
[O:1]=[S:2]1(=[O:10])[CH2:6][CH2:5][CH:4]([C:7](O)=[O:8])[CH2:3]1>O1CCCC1>[O:1]=[S:2]1(=[O:10])[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
1,1-Dioxo-tetrahydrothiophene-3-carboxylic acid (300 mg) is dissolved in dry tetrahydrofuran (10 mL). The reaction mixture is cooled to 0° C. and borane tetrahydrofuran complex (2 mL) is added dropwise. After stirring for 1 hour at 0° C., the mixture is concentrated under vacuum, partitioned between dichloromethane and water. The organic phase is dried (MgSO4) and concentrated to give the title compound. Yield: 250 mg.
Workup
- additionborane tetrahydrofuran complex (2 mL) is added dropwise
- concentrationthe mixture is concentrated under vacuum
- custompartitioned between dichloromethane and water
- dry with materialThe organic phase is dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-275bf53a13bc4994b56691c0fda17c2f
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642585B2
Reaction notes
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