Phthalimide → 2-Phenyl-4-(4-phtalimidobut-1-yl)-1,3-dioxolane

HRID 225411

반응식

HRID 225411 반응식
N(C(OCC)=O)=NC(OCC)=O.[C:13]1([CH:19]2[O:23][CH:22]([CH2:24][CH2:25][CH2:26][CH2:27]O)[CH2:21][O:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:48]1(=[O:58])[NH:52][C:51](=[O:53])[C:50]2=[CH:54][CH:55]=[CH:56][CH:57]=[C:49]12>C1COCC1>[C:13]1([CH:19]2[O:23][CH:22]([CH2:24][CH2:25][CH2:26][CH2:27][N:52]3[C:51](=[O:53])[C:50]4=[CH:54][CH:55]=[CH:56][CH:57]=[C:49]4[C:48]3=[O:58])[CH2:21][O:20]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

6

반응물 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2366801,3-Dioxolane-4-butanol, 2-phenyl-

생성물 1

HCID 224927812-Phenyl-4-(4-phtalimidobut-1-yl)-1,3-dioxolane수율 92.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of diethyl azodicarboxylate (8.6 g, 49.4 mmol) in 40 mL of THF was slowly added to a cold (ice bath) solution of 17 (10.0 g, 45.0 mmol), triphenylphosphine (13.0 g, 49.5 mmol) and phthalimide (7.3 g, 49.7 mmol) in 60 mL of THF. After being kept at ambient temperature overnight, the solution was concentrated and the residue was triturated with ether (˜150 mL) to precipitate triphenylphosphine oxide which was then removed by filtration. The filtrate was concentrated to give an oily residue which was chromatographed on silica eluting with 33% ethyl acetate in hexane. Concentration of the pure product fractions followed by drying under vacuum afforded 14.6 g (92%) of the desired product as a semi-solid (a mixture of diastereomers): 1H NMR (CDCl3, 300 MHz, ppm) 7.85 (m, 2H), 7.71 (m, 2H), 7.46 (m, 2H), 7.36 (m, 3H), 5.90 (s, 0.4H), 5.78 (s, 0.6H), 4.3-4.0 (m, 2H), 3.68 (m, 3H), 1.9-1.3 (m, 6H).

후처리

  1. concentrationthe solution was concentrated
  2. customthe residue was triturated with ether (˜150 mL)
  3. customto precipitate triphenylphosphine oxide which
  4. customwas then removed by filtration
  5. concentrationThe filtrate was concentrated
  6. customto give an oily residue which
  7. customwas chromatographed on silica eluting with 33% ethyl acetate in hexane
  8. customby drying under vacuum

출처 및 근거

ORD 기록
ord-be17f73fdacd4c4bb2f29178dcd0b3d6
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07556923B1

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