Diethyl Ether → 4-(Acetylthiomethyl)tetrahydropyran

HRID 73235

반응식

HRID 73235 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 597040184-(Acetylthiomethyl)tetrahydropyran수율 86.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-881dc1cf740344e7acd0e46939433be5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829034B2

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