m-Chloroperbenzoic acid → HCID 85344768, compound

HRID 1640545Notes

Reaction equation

HRID 1640545 reaction equation
[CH2:1]([O:8][C:9](=[O:15])[NH:10][CH2:11][CH2:12][CH:13]=[CH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:24])C=1>C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9](=[O:15])[NH:10][CH2:11][CH2:12][CH:13]1[CH2:14][O:24]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14688338Benzyl but-3-en-1-ylcarbamate

Product 1

HCID 85344768HCID 85344768, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of but-3-enyl-carbamic acid benzyl ester (prepared according to Heterocycles (2006), 67(2), 549-554; 21.5 g, 105 mmol) in chloroform (380 mL) was added, dropwise over a period of 1 h, a solution of MCPBA (28.3 g, 1.1 eq.) in chloroform (270 mL) at 10° C. Stirring was continued for 20 h at rt. The reaction mixture was filtered and 10% sodium sulfite solution was added to the filtrate (until starch-iodide paper test was negative). The mixture was washed with 5% Na2CO3 and brine. The org. layer was dried over MgSO4 and concentrated to afford the title intermediate as a colourless liquid (21.6 g, 93% yield).

Workup

  1. customat 10° C
  2. filtrationThe reaction mixture was filtered
  3. addition10% sodium sulfite solution was added to the filtrate (until starch-iodide paper test was negative)
  4. washThe mixture was washed with 5% Na2CO3 and brine
  5. dry with materiallayer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f939ae5008a94602871ce13082daf75a
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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