Phthalimide → HCID 14499629, compound

HRID 1199732Notes

Reaction equation

HRID 1199732 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.O[CH:32]([CH2:35][CH2:36][CH:37]([N:40]1[C:44](=[O:45])[C:43]2=[CH:46][CH:47]=[CH:48][CH:49]=[C:42]2[C:41]1=[O:50])[CH2:38][F:39])[CH:33]=[CH2:34].CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O>[F:39][CH2:38][CH:37]([N:40]1[C:41](=[O:50])[C:42]2=[CH:49][CH:48]=[CH:47][CH:46]=[C:43]2[C:44]1=[O:45])[CH2:36][CH2:35][CH:32]([N:24]1[C:20](=[O:30])[C:21]2=[CH:29][CH:28]=[CH:27][CH:26]=[C:22]2[C:23]1=[O:25])[CH:33]=[CH2:34]

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 14499628HCID 14499628, compound

Product 1

HCID 14499629HCID 14499629, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of triphenylphosphine (103 g, 0.39 mol), phthalimide (57.8 g, 0.43 mol) and 3-hydroxy-7-fluoro-6-phthalimidoheptene (109 g, 0.39 mol) in dry THF (2 L) under nitrogen, was added dropwise a solution of diethylazodicarboxylate (75.4 g, 0.43 mol) in dry THF (1 L). The solution was kept <20° C. The reaction mixture was stirred for 72 hours. The THF layer was separated and evaporated to give an oil which was boiled in water (5×250 mL), the water was decanted and the residue was dissolved in dichloromethane. After washing with water, the organic phase was separated, dried over Na2SO4 and evaporated to eliminate triphenylphosphine oxide. Evaporation of the ether phase and chromatography of the residue (200 g) on silica gel (1.5 kg), elution with petroleum ether/ethyl acetate (2:3) afforded the title compound (8, R=--CH2F) as a white solid: 36.4 g (22.8%). TLC PE/EtOAc 1:1, Rf=0.78. NMR (1H, CDCl3, 90 MHz).

Workup

  1. customwas kept <20° C
  2. customThe THF layer was separated
  3. customevaporated
  4. customto give an oil which
  5. customthe water was decanted
  6. dissolutionthe residue was dissolved in dichloromethane
  7. washAfter washing with water
  8. customthe organic phase was separated
  9. dry with materialdried over Na2SO4
  10. customevaporated
  11. customEvaporation of the ether phase and chromatography of the residue (200 g)
  12. washon silica gel (1.5 kg), elution with petroleum ether/ethyl acetate (2:3)

Sources & evidence

ORD record
ord-eb84eb53fefb49c5bcca9b444e1bbd1d
Source dataset
uspto-grants-1990_02
Patent number
US04902719

Reaction notes

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