Sulfuryl chloride → HCID 10922235, compound

HRID 1963022Notes

Reaction equation

HRID 1963022 reaction equation
[O:1]=[C:2]([CH3:14])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].S(Cl)([Cl:18])(=O)=O>C(Cl)(Cl)Cl>[Cl:18][CH:3]([C:2](=[O:1])[CH3:14])[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 142266Benzyl acetoacetate

Product 1

HCID 10922235HCID 10922235, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of benzyl 3-oxobutanoate (15 g, 78 mmol) in chloroform (150 mL) at 0° C. was added sulfuryl chloride (6.35 mL, 78 mmol) during a period of 20 min. The ice bath was removed and reaction mixture was allowed to warm to room temperature and stirred for 4 h. The solvent was evaporated and the crude product was diluted with EtOAc (250 mL). The organic layer was washed with H2O (100 mL), separated, dried over MgSO4 and concentrated to give the desired product as a light yellow oil (17.6 g, 99% yield). 1H NMR (CDCl3) δ 2.31 (s, 3H), 4.80 (s, 1H), 5.25 (s, 2H), 7.30-7.42 (m, 5H). LCMS, [M−H]+=225.4.

Workup

  1. customThe ice bath was removed
  2. customreaction mixture
  3. customThe solvent was evaporated
  4. additionthe crude product was diluted with EtOAc (250 mL)
  5. washThe organic layer was washed with H2O (100 mL)
  6. customseparated
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dcf29df94a1a4a208c28f00117ca2423
Source dataset
uspto-grants-2013_04
Patent number
US08415386B2

Reaction notes

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