Phthalimide → HCID 59703765, compound

HRID 908623Notes

Reaction equation

HRID 908623 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:13]O)[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:10])([F:11])[F:12])[CH2:13][N:19]1[C:15](=[O:25])[C:16]2[C:17](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:18]1=[O:20]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 17750671[3-Fluoro-4-(trifluoromethoxy)phenyl]methanol

Product 1

HCID 59703765HCID 59703765, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound (2.95 g) obtained in Step 1 in THF (30 ml) were added phthalimide (3.10 g) and triphenylphosphine (5.52 g) with stirring at room temperature, and the mixture was stirred under ice-cooling. With stirring under ice-cooling, diisopropyl azodicarboxylate (4.15 ml) was added, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=2:8-3:7) to give the title compound (4.30 g).

Workup

  1. stirringthe mixture was stirred under ice-
  2. temperaturecooling
  3. stirringWith stirring under ice-
  4. temperaturecooling
  5. stirringthe mixture was stirred overnight at room temperature
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=2:8-3:7)

Sources & evidence

ORD record
ord-03b533f1faea4c4d84bb7ed373ce2520
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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