N-Hydroxyphthalimide → 2-(Cyclopent-3-enyloxy)isoindoline-1,3-dione

HRID 1614067ノート

反応式

HRID 1614067 の反応式
[CH:1]1([OH:6])[CH2:5][CH:4]=[CH:3][CH2:2]1.O[N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH:1]1([O:6][N:8]2[C:9](=[O:18])[C:10]3=[CH:17][CH:16]=[CH:15][CH:14]=[C:11]3[C:12]2=[O:13])[CH2:5][CH:4]=[CH:3][CH2:2]1

参加物

6

反応物 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2814783-Cyclopenten-1-ol

生成物 1

HCID 197740932-(Cyclopent-3-enyloxy)isoindoline-1,3-dione収率 61.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
45 °C

実験手順

To a solution of 3-cyclopenten-1-ol (15.3 g), N-hydroxyphthalimide (29.7 g) and triphenylphosphine (47.7 g) in tetrahydrofuran (250 ml) was added diethyl azodicarboxylate (31.7 g) at 40° to 50° C. After stirring at 45° C. for 2 hours, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The separated organic layer was washed with 5% aqueous solution of sodium bicarbonate, brine, successively and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residual oil was subjected to column chromatography on silica gel. The desired product was eluted with 15% ethyl acetate in n-hexane to give N-(3-cyclopenten-1-yloxy)phthalimide (25.6 g).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe separated organic layer was washed with 5% aqueous solution of sodium bicarbonate, brine
  3. dry with materialsuccessively and dried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. washThe desired product was eluted with 15% ethyl acetate in n-hexane

出典と根拠

ORDレコード
ord-149b2c5b5ccb41d99ccc5a2f9791eeaa
出典データセット
uspto-grants-1993_03
特許番号
US05194432

反応ノート

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