Phthalimide → HCID 12290030, compound

HRID 1824775Notes

Reaction equation

HRID 1824775 reaction equation
[CH3:1][CH:2](O)[CH2:3][CH:4]=[CH2:5].[C:7]1(=[O:17])[NH:11][C:10](=[O:12])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.O>[CH2:1]=[CH:2][CH2:3][CH:4]([N:11]1[C:7](=[O:17])[C:8]2=[CH:16][CH:15]=[CH:14][CH:13]=[C:9]2[C:10]1=[O:12])[CH3:5]

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 122474-Penten-2-OLHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 12290030HCID 12290030, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-penten-2-ol (5.00 g, 58.1 mmol), phthalimide (8.55 g, 58.1 mmol), and triphenylphosphine (15.2 g, 58.1 mmol) in THF (40 mL), at 0° C. under nitrogen, was added a solution of diethyl azodicarboxylate (10.1 g, 58.1 mmol) in THF (20 mL) dropwise. The mixture was stirred at 0° C. (12 h) and then at 25° (12 h). The mixture was diluted with water and extracted three times with chloroform. The chloroform extracts were dried (Na2SO4), evaporated and column chromatographed on Merck silica gel 60 (70–230 mesh) with chloroform to give 8.77 g (70.2% yield) of colorless oil.

Workup

  1. customat 25°
  2. custom(12 h)
  3. extractionextracted three times with chloroform
  4. dry with materialThe chloroform extracts were dried (Na2SO4)
  5. customevaporated
  6. customcolumn chromatographed on Merck silica gel 60 (70–230 mesh) with chloroform

Sources & evidence

ORD record
ord-cb1d762b2e084f36a3c2705318a6738b
Source dataset
uspto-grants-2006_05
Patent number
US07045538B2

Reaction notes

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