Ethyl Acetate → HCID 22325252, compound

HRID 1604504Notes

Reaction equation

HRID 1604504 reaction equation
C([C:5]([Br:17])(CCCC)[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)CCC.C1C=C(Cl)C=C(C(OO)=O)C=1.[S:29]([O-])([O-:31])=[O:30].[Na+].[Na+].C(OCC)(=O)C>C(Cl)Cl>[S:29](=[C:5]([Br:17])[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)(=[O:31])=[O:30]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 22678860HCID 22678860, compound

Product 1

HCID 22325252HCID 22325252, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8.5 g (25 mmol) of sulfide obtained from Step 3 in 200 mL of CH2Cl2 at 0° C. was added 15.9 g (60 mmol) of mCPBA (64% peracid). The resulting solution was stirred cold for 10 min, then was allowed to stirred ambient temperature for 5 hours. To the mixture was added 10% solution of sodium sulfite and ethyl acetate. The extract was washed several times with saturated Na2CO3, dried (MgSO4), and concentrated in vacuo to give 10.2 g (98%) of the desired product as a colorless oil: 1H NMR (CDCl3) d 0.91 (t, J=7.05 Hz, 6H), 1.03-1.4 (m, 8H), 1.65-1.82 (m, 2H), 1.90-2.05 (m, 2H), 3.54 (s, 2H), 5.01 (s, 2H), 7.04-7.23 (m, 1H), 7.30 (dd, J=8.87, 2.42 Hz, 1H), 8.03 (dd, J 8.86, 5.64, 1H), 9.49 (s, 1H).

Workup

  1. stirringto stirred ambient temperature for 5 hours
  2. washThe extract was washed several times with saturated Na2CO3
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05c3bcb66b80482c837a67931b495bd1
Source dataset
uspto-grants-1999_11
Patent number
US05994391

Reaction notes

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