Cesium carbonate → 3-(3-Hydroxypropylsulfanyl)-dihydrofuran-2-one

HRID 1987820Notes

Reaction equation

HRID 1987820 reaction equation
[SH:1][CH2:2][CH2:3][CH2:4][OH:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:13]1[CH2:17][CH2:16][O:15][C:14]1=[O:18]>CC(C)=O>[OH:5][CH2:4][CH2:3][CH2:2][S:1][CH:13]1[CH2:17][CH2:16][O:15][C:14]1=[O:18]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 882113-MercaptopropanolHCID 954632(3H)-Furanone, 3-bromodihydro-

Product 1

HCID 661156623-(3-Hydroxypropylsulfanyl)-dihydrofuran-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Mercaptopropan-1-ol (1.61 g, 17.4 mmol) was dissolved in acetone (40 mL) followed by addition of cesium carbonate (5.67 g, 17.4 mmol) and 3-bromo-dihydrofuran-2(3H)-one (1.63 ml, 17.4 mmol). The suspension was stirred vigorously for 40 hours. The reaction was filtered through silica gel, rinsed with acetone and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 70-80% ethyl acetate/hexanes. Recovered the desired product as an oil (2.1 g, 71%).

Workup

  1. filtrationThe reaction was filtered through silica gel
  2. washrinsed with acetone
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with 70-80% ethyl acetate/hexanes
  5. customRecovered the desired product as an oil (2.1 g, 71%)

Sources & evidence

ORD record
ord-aa0f3a900ece41a7b4a32194578dc77a
Source dataset
uspto-grants-2009_06
Patent number
US07553842B2

Reaction notes

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