N-Hydroxyphthalimide → 2-(1-Hydroxymethyl-cyclopropylmethoxy)-isoindole-1,3-dione

HRID 2218442

反応式

HRID 2218442 の反応式
[OH:1][CH2:2][C:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.O[N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[OH:1][CH2:2][C:3]1([CH2:6][O:7][N:9]2[C:13](=[O:14])[C:12]3[C:11](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]2=[O:19])[CH2:5][CH2:4]1

参加物

6

反応物 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 41014371,1-Bis(hydroxymethyl)cyclopropane

生成物 1

HCID 692205082-(1-Hydroxymethyl-cyclopropylmethoxy)-isoindole-1,3-dione収率 57%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

(1-Hydroxymethyl-cyclopropyl)-methanol (4.08 g, 0.04 mol), N-hydroxyphthalimide (6.53 g, 0.04 mol) and triphenylphosphine (10.50 g, 0.04 mol) were combined in anhydrous tetrahydrofuran (100 mL) and stirred at 0° C. for 1.5 hours. Diethyl azodicarboxylate (6.97 g, 0.04 mol) was added at 0° C. and the reaction mixture was stirred at room temperature overnight. Repeated concentration of the reaction mixture from chloroform and filtration of the resulting precipitate (triphenylphosphine oxide) afforded the crude product which was further purified by silica gel chromatography. Elution with hexane/ethyl acetate (3:2) provided 2-(1-Hydroxymethyl-cyclopropylmethoxy)-isoindole-1,3-dione (5.63 g, 57% yield) as a white solid: 1H NMR (400 MHz; CDCl3) δ 7.82-7.85 (2H, m), 7.74-7.78 (2H, m), 4.19 (2H, s), 3.72 (2H, s), 0.63 (4H, s)

後処理

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. filtrationfrom chloroform and filtration of the resulting precipitate (triphenylphosphine oxide)
  3. customafforded the crude product which
  4. customwas further purified by silica gel chromatography
  5. washElution with hexane/ethyl acetate (3:2)

出典と根拠

ORDレコード
ord-18a0eca0641945b884f885252e04965b
出典データセット
uspto-grants-2008_08
特許番号
US07411001B2

関連ノート

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