3a,4,5,7a-Tetrahydro-2-benzofuran-1,3-dione → N-[4-chloro-2-fluoro-5-ethoxymethylphenyl]-3,4,5,6-tetrahydrophthalimide

HRID 231421ノート

反応式

HRID 231421 の反応式
[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]=1

参加物

3

反応物 2

HCID 127266013a,4,5,7a-Tetrahydro-2-benzofuran-1,3-dioneHCID 200323714-Chloro-5-ethoxymethyl-2-fluoroaniline2 回

生成物 1

HCID 13896447N-[4-chloro-2-fluoro-5-ethoxymethylphenyl]-3,4,5,6-tetrahydrophthalimide

実験手順

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.

後処理

  1. customAcetic acid was removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
  3. washwashed successively with a saturated aqueous solution of sodium bicarbonate (5×50 ml)
  4. dry with materialThe dried (magnesium sulfate) organic layer
  5. concentrationwas concentrated under reduced pressure
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-99194ebf48d840dbbb3c193f203d8c46
出典データセット
uspto-grants-1989_07
特許番号
US04846882

反応ノート

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