Diethyl Ether → (3aRS,7aRS)-2-[1-Ethoxy-2-(2-methoxyphenyl)ethylidene]-4-oxo-7,7-diphenylperhydroisoindolium tetrafluoroborate

HRID 1196271Notes

Reaction equation

HRID 1196271 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[CH2:6]([O+](CC)CC)[CH3:7].[C:13]1([C:19]2([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH:27]3[CH:23]([CH2:24][N:25]([C:28](=[O:38])[CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[O:36][CH3:37])[CH2:26]3)[C:22](=[O:39])[CH2:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCOCC>ClCCl>[F:1][B-:2]([F:5])([F:4])[F:3].[CH2:6]([O:38][C:28](=[N+:25]1[CH2:24][CH:23]2[CH:27]([C:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:20][CH2:21][C:22]2=[O:39])[CH2:26]1)[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][CH3:37])[CH3:7]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2723982Triethyloxonium tetrafluoroborateHCID 67915851(3aRS,7aRS)-7,7-Diphenyl-2-[(2-methoxyphenyl)acetyl]perhydro-4-isoindolone

Product 1

HCID 86745794(3aRS,7aRS)-2-[1-Ethoxy-2-(2-methoxyphenyl)ethylidene]-4-oxo-7,7-diphenylperhydroisoindolium tetrafluoroborateYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethyloxonium tetrafluoroborate (2.35 g) is added to a solution of (3aRS,7aRS)-7,7-diphenyl-2-[(2-methoxyphenyl)acetyl]perhydro-4-isoindolone (5 g) in dichloromethane (10 cc). The reaction mixture is left stirring for 20 hours at room temperature; it is then treated with ether (100 cc) and the precipitate obtained is drained, washed with ether (100 cc) and dried. (3aRS,7aRS)-2-[1-Ethoxy-2-(2-methoxyphenyl)ethylidene]-4-oxo-7,7-diphenylperhydroisoindolium tetrafluoroborate (5.75 g) is obtained in the form of a yellow powder, which is used in the crude state for the following manipulation.

Workup

  1. waitThe reaction mixture is left
  2. customthe precipitate obtained
  3. washwashed with ether (100 cc)
  4. customdried

Sources & evidence

ORD record
ord-8f5113216e814ade8b2519aca94f98b6
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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