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

HRID 1257973Notes

Reaction equation

HRID 1257973 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-854b9ff3a3e048c4b155094d66bc0dd4
Source dataset
uspto-grants-2013_06
Patent number
US08465921B2

Reaction notes

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