Phthalimide → HCID 12290030, compound

HRID 489778Notes

Reaction equation

HRID 489778 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° C. (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° C.
  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-9d94d456d1bb43cbbec010081b8da8b6
Source dataset
uspto-grants-2005_12
Patent number
US06979695B2

Reaction notes

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