Hydrochloric Acid → (+)-5,6-Dimethoxy-2-[2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]isoindoline hydrochloride

HRID 272339Notes

Reaction equation

HRID 272339 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH2:8][N:7]([C:14]1[C:15]([CH3:34])=[C:16]([CH3:33])[C:17]3[O:21][C:20]([CH3:23])([CH3:22])[CH:19]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=4)[C:18]=3[C:31]=1[CH3:32])[CH2:6]2.[ClH:35]>C(OCC)(=O)C>[ClH:35].[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH2:8][N:7]([C:14]1[C:15]([CH3:34])=[C:16]([CH3:33])[C:17]3[O:21][C:20]([CH3:23])([CH3:22])[CH:19]([C:24]4[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=4)[C:18]=3[C:31]=1[CH3:32])[CH2:6]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 99119865,6-Dimethoxy-2-[2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]isoindoline

Product 1

HCID 21961359(+)-5,6-Dimethoxy-2-[2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]isoindoline hydrochlorideYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(+)-5,6-Dimethoxy-2-[2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl]isoindoline (296 mg, 0.65 mmol) was dissolved in ethyl acetate (5.0 ml) and then a 4 N solution of hydrogen chloride in ethyl acetate (0.38 ml) was added into this mixture. The solvent was removed under reduced pressure and the residue was crystallized from a mixed solution of ethyl acetate and diethyl ether (1:5). The crystals were collected by filtration and washed with a cold mixed solution of ethyl acetate and diethyl ether (1:5) to obtain 291 mg (87% yield) of the titled compound as a crystalline product. Melting point: 170-171° C. [α]D=+44.9° (c=0.495, chloroform)

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was crystallized from a mixed solution of ethyl acetate and diethyl ether (1:5)
  3. filtrationThe crystals were collected by filtration
  4. washwashed with a cold mixed solution of ethyl acetate and diethyl ether (1:5)

Sources & evidence

ORD record
ord-604b9182627a4e398745ab05bc8ab1e0
Source dataset
uspto-grants-2008_11
Patent number
US07456162B2

Reaction notes

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