Vinyl chloroformate → (3aRS,7aRS)-7,7-bis(3-chlorophenyl)-2-vinyloxycarbonylperhydro-4-isoindolone

HRID 1196248Notes

Reaction equation

HRID 1196248 reaction equation
C([N:8]1[CH2:16][CH:15]2[CH:10]([C:11]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[CH2:12][CH2:13][C:14]2=[O:17])[CH2:9]1)C1C=CC=CC=1.Cl[C:33]([O:35][CH:36]=[CH2:37])=[O:34]>ClCCCl.C(OC(C)C)(C)C>[Cl:31][C:27]1[CH:26]=[C:25]([C:11]2([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[CH:10]3[CH:15]([CH2:16][N:8]([C:33]([O:35][CH:36]=[CH2:37])=[O:34])[CH2:9]3)[C:14](=[O:17])[CH2:13][CH2:12]2)[CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 78808Vinyl chloroformateHCID 67915832HCID 67915832, compound

Product 1

HCID 67915885(3aRS,7aRS)-7,7-bis(3-chlorophenyl)-2-vinyloxycarbonylperhydro-4-isoindolone

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 7914Diisopropyl EtherSolvent

Procedure

A solution of (3aRS,7aRS)-2-benzyl-7,7-bis(3-chlorophenyl)perhydro-4-isoindolone (11.5 g) in 1,2-dichloroethane (250 cc) is treated with vinyl chloroformate (2.8 cc) and heated to reflux for 16 hours, then concentrated under reduced pressure (2.7 kPa). The residue is chromatographed on a column of silica gel (particle size 0.04-0.063 mm, diameter 6 cm, height 32 cm), eluting under a nitrogen pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (80:20) and collecting 25-cc fractions. Fractions 19 to 27 are combined and concentrated to dryness under reduced pressure (2.7 kPa). The meringue-like product obtained is solidified in isopropyl ether and the precipitate is drained, washed with isopropyl ether and dried to give (3aRS,7aRS)-7,7-bis(3-chlorophenyl)-2-vinyloxycarbonylperhydro-4-isoindolone (6.7 g) in the form of a white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. concentrationconcentrated under reduced pressure (2.7 kPa)
  4. customThe residue is chromatographed on a column of silica gel (particle size 0.04-0.063 mm, diameter 6 cm, height 32 cm)
  5. washeluting under a nitrogen pressure of 0.5 bar
  6. additionwith a mixture of cyclohexane and ethyl acetate (80:20)
  7. customcollecting 25-cc fractions
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  9. customThe meringue-like product obtained
  10. washwashed with isopropyl ether
  11. customdried

Sources & evidence

ORD record
ord-e978a1f3982c4d8c886ad1e7a2517547
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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