Potassium ethanethioate → HCID 59268001, compound

HRID 1809400Notes

Reaction equation

HRID 1809400 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)(=O)=O)=CC=1.[C:19]([O-:22])(=[S:21])[CH3:20].[K+]>CN(C=O)C.C(OCC)(=O)C>[O:14]1[CH2:15][CH2:16][CH2:17][CH2:18][C@H:13]1[CH2:12][S:21][C:19](=[O:22])[CH3:20]

Participants

5

Reactant 2

HCID 23670855Potassium ethanethioateHCID 51900550HCID 51900550, compound

Product 1

HCID 59268001HCID 59268001, compoundYield 111.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.90 g (14.41 mmol) of (2S)-oxan-2-ylmethyl 4-methylbenzene-1-sulfonate in DMF (40 mL) are added 3.29 g (28.83 mmol) potassium thioacetate at room temperature. After complete addition, the reaction is stirred at room temperature for 18 h, then heated to 50° C. for further 20 h. The reaction mixture is diluted with ethyl acetate (250 mL) and washed with saturated aqueous NaHCO3 solution (2×100 mL) and water (2×100 mL). The organic layer is dried (MgSO4), filtered and the filtrate is concentrated under reduced pressure to afford 2.79 g of 1-{[(2S)-oxan-2-ylmethyl]sulfanyl}ethan-1-one. Yield: 93%; ES-MS: m/z 175 [M+H]; 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.17-1.36 (2H, m), 1.42-1.59 (2H, m), 1.63-1.72 (1H, m), 1.79-1.88 (1H, m), 2.34 (3H, s), 2.84-2.93 (1H, m), 3.10 (1H, dd, J=13.73, 4.27 Hz), 3.30-3.47 (2H, m), 3.98 (1H, dt, J=11.41, 2.08 Hz).

Workup

  1. additionAfter complete addition
  2. temperatureheated to 50° C. for further 20 h
  3. washwashed with saturated aqueous NaHCO3 solution (2×100 mL) and water (2×100 mL)
  4. dry with materialThe organic layer is dried (MgSO4)
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-e5206d4a2f6a4d35a29ea0868f50967e
Source dataset
uspto-grants-2013_01
Patent number
US08362039B2

Reaction notes

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