Diethyl Ether → 4-(Acetylthiomethyl)tetrahydropyran

HRID 73235

Reaction equation

HRID 73235 reaction equation
Br[CH2:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[C:9]([O-:12])(=[S:11])[CH3:10].[K+].C(OCC)C>CN(C=O)C>[O:6]1[CH2:7][CH2:8][CH:3]([CH2:2][S:11][C:9](=[O:12])[CH3:10])[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 27732864-(Bromomethyl)oxaneHCID 23670855Potassium ethanethioate

Product 1

HCID 597040184-(Acetylthiomethyl)tetrahydropyranYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.97 g (5.4 mmol) of 4-bromomethyl tetrahydropyran in DMF (9.7 mL) were added 1.27 g (11.2 mmol) of potassium thioacetate. The reaction was stirred at room temperature for 3 h. Diethyl ether (100 mL) was added and the reaction mixture was washed with saturated aqueous NaHCO3 solution (2×25 mL) and brine (25 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica, eluent: heptanes, 10% ethyl acetate) to afford 0.81 g of thioacetic acid S-(tetrahydro-pyran-4-ylmethyl)ester.

Workup

  1. washthe reaction mixture was washed with saturated aqueous NaHCO3 solution (2×25 mL) and brine (25 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica, eluent: heptanes, 10% ethyl acetate)

Sources & evidence

ORD record
ord-881dc1cf740344e7acd0e46939433be5
Source dataset
uspto-grants-2014_09
Patent number
US08829034B2

Linked notes

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