3a,4,5,7a-Tetrahydro-2-benzofuran-1,3-dione → N-[4-chloro-2-fluoro-5-ethoxymethylphenyl]-3,4,5,6-tetrahydrophthalimide
Reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[CH:3]2[CH2:7][CH2:8][CH:9]=[CH:10][CH:2]12.[Cl:12][C:13]1[C:19]([CH2:20][O:21][CH2:22][CH3:23])=[CH:18][C:16]([NH2:17])=[C:15]([F:24])[CH:14]=1>>[Cl:12][C:13]1[C:19]([CH2:20][O:21][CH2:22][CH3:23])=[CH:18][C:16]([N:17]2[C:1](=[O:11])[C:2]3[CH2:10][CH2:9][CH2:8][CH2:7][C:3]=3[C:4]2=[O:6])=[C:15]([F:24])[CH:14]=1Participants
Procedure
Tetrahydrophthalic anhydride (0.58 g, 0.0039 mole), and 4-chloro-5-ethoxymethyl-2-fluoroaniline in glacial acetic acid from Step C was heated at 100° C. overnight. Acetic acid was removed under reduced pressure. The residue was dissolved in ethyl acetate (100 ml) and washed successively with a saturated aqueous solution of sodium bicarbonate (5×50 ml) and a 10% aqueous solution of hydrochloric acid. The dried (magnesium sulfate) organic layer was concentrated under reduced pressure. The residue was passed through a column of silica gel eluting with ethyl acetate:heptane (3:17). Appropriate fractions were combined and concentrated under reduced pressure yielding N-[4-chloro-2-fluoro-5-ethoxymethylphenyl]-3,4,5,6-tetrahydrophthalimide as an amber solid, m.p. 89°-91° C. The nmr spectrum was consistent for the proposed structure.
Workup
- customAcetic acid was removed under reduced pressure
- dissolutionThe residue was dissolved in ethyl acetate (100 ml)
- washwashed successively with a saturated aqueous solution of sodium bicarbonate (5×50 ml)
- dry with materialThe dried (magnesium sulfate) organic layer
- concentrationwas concentrated under reduced pressure
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-99194ebf48d840dbbb3c193f203d8c46
- Source dataset
- uspto-grants-1989_07
- Patent number
- US04846882
Reaction notes
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