Sulfuryl chloride → HCID 86667468, compound

HRID 2402014Notes

Reaction equation

HRID 2402014 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1.S(Cl)([Cl:20])(=O)=O>C(Cl)Cl>[Cl:20][CH:10]([C:9](=[O:16])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 10847663Ethyl 4-(4-chlorophenyl)-3-oxobutanoate

Product 1

HCID 86667468HCID 86667468, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 4-(4-chlorophenyl)-3-oxobutanoate (61.0 g, 253 mmol) in DCM (811 mL) in an ice bath was added sulfuryl chloride (34.2 g, 253 mmol) and the resulting solution was allowed to stir at room temperature overnight. The reaction was quenched with saturated sodium bicarbonate solution (200 mL) and the layers separated. The organic layer was washed with brine (100 mL), dried over MgSO4, filtered, and concentrated in vacuo to give 70.8 g of title compound. (100% yield). 1H NMR (400 MHz, CDCl3) δ: 7.33-7.30 (m, 2H), 7.17-7.14 (m, 2H), 4.85 (s, 1H), 4.26 (dq, 1H, J=7.2, 1.2 Hz), 4.02 (d, 1H, J=16.8 Hz), 3.97 (d, J=16.8 Hz, 1H), 1.29 (t, 3H, J=7.2 Hz).

Workup

  1. customThe reaction was quenched with saturated sodium bicarbonate solution (200 mL)
  2. customthe layers separated
  3. washThe organic layer was washed with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac44984159a74d23b09940f3cdb78d0e
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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