Furfuryl Alcohol → Methanesulfonic acid furan-2-ylmethyl ester
Reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][OH:7].C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl>[CH3:15][S:16]([O:7][CH2:6][C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)(=[O:18])=[O:17]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To the solution of furan-2-ylmethanol (500 mg, 5.1 mmol) in CH2Cl2 (10 mL) and triethylamine (1.54 g, 15.3 mmol) at 0° C. was added dropwise methanesulfonyl chloride (695 mg, 6.1 mmol). The mixture was stirred at 0° C. for 15 min and was quenched with 10 mL of water. The layers were separated and the aqueous layer was extracted with CH2Cl2 (1×10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the title compound.
Workup
- customwas quenched with 10 mL of water
- customThe layers were separated
- extractionthe aqueous layer was extracted with CH2Cl2 (1×10 mL)
- dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-e49580dd74364160a354a59d3be2d06e
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158663B2
Reaction notes
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