Phthalimide → HCID 117835768, compound

HRID 1844295Notes

Reaction equation

HRID 1844295 reaction equation
[CH2:1]([CH:4]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][CH:5]1[CH2:11]O)[CH:2]=[CH2:3].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.[C:44]1(=[O:54])[NH:48][C:47](=[O:49])[C:46]2=[CH:50][CH:51]=[CH:52][CH:53]=[C:45]12>C1COCC1>[CH2:1]([CH:4]1[O:8][C:7]([CH3:9])([CH3:10])[O:6][CH:5]1[CH2:11][N:48]1[C:44](=[O:54])[C:45]2[C:46](=[CH:50][CH:51]=[CH:52][CH:53]=2)[C:47]1=[O:49])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 21061831HCID 21061831, compound

Product 1

HCID 117835768HCID 117835768, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of compound 2 (2.8 g, 16.3 mmol) in THF (120 mL) were added PPh3 (6.4 g, 24.4 mmol) and DEAD (40% in toluene, 10.6 mL, 24.3 mmol) at 0° C. After 20 min stirring, phthalimide (3.59 g, 24.4 mmol). The reaction mixture was stirred overnight at room temperature, concentrated, diluted with EtOAc (300 mL) and extracted with aq. NaHCO3 solution (100 mL). The organic layer was dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc=2/1) to give compound 3 (4.74 g, 15.7 mmol, 97%) as an oil. 1H NMR (CDCl3, 300 MHz) δ 7.80-7.85 (m, 2H), 7.68-7.73 (m, 2H), 5.82 (m, 1H), 5.13-5.24 (m, 2H), 4.48 (m, 1H), 4.26 (m, 1H), 3.90 (dd, 1H, J=10.5, 13.5), 3.52 (dd, 1H, J=3.0, 13.5), 2.37-2.57 (m, 2H), 1.53, 1.30 (2s, 6H); 13C NMR (CDCl3, 75 MHz) δ 168.5, 134.1, 133.9, 132.4, 123.5, 118.0, 109.1, 76.5, 74.3, 39.1, 33.5, 28.2, 26.1.

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. concentrationconcentrated
  3. additiondiluted with EtOAc (300 mL)
  4. extractionextracted with aq. NaHCO3 solution (100 mL)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (Hex/EtOAc=2/1)

Sources & evidence

ORD record
ord-04e11698f50a49ad97e9b6f657ac5375
Source dataset
uspto-grants-2015_02
Patent number
US08946397B1

Reaction notes

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