Isopropanol → HCID 4017380, compound

HRID 1947649Notes

Reaction equation

HRID 1947649 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[NH:10][C:8](=[O:9])[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2].[C:15]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:20]=CC=C[CH:16]=1.C(O)(C)C.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.C(OCC)(=O)C.O>[CH:15]([N:10]1[C:11](=[O:12])[C:6]2[C:7](=[CH:13][CH:14]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:8]1=[O:9])([CH3:20])[CH3:16]

Participants

8

Reactant 4

HCID 3776IsopropanolHCID 69694-NitrophthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 4017380HCID 4017380, compoundYield 52.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-nitrophthalimide (2.0 g, 10.41 mmol), triphenylphosphine (11.45 mmol, 2.99 g) and iso-propanol (11.45 mmol, 0.73 ml) in anhydrous THF (40 ml) was added diisopropylazodicarboxylate (2.37 g, 11.45 mmol) and the reaction stirred for 16 hrs at room temperature. Water and ethyl acetate were added and the organic phase separated, washed with brine, then dried (MgSO4) and evaporated in vacuo. The crude residue was purified by flash column chromatography (30% ethyl acetate in petroleum ether) to afford the title compound as a pale yellow solid (1.27 g, 52%). HPLC retention time 4.60 min. Mass spectrum (ES+) m/z 235 (M+H).

Workup

  1. customthe organic phase separated
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe crude residue was purified by flash column chromatography (30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-9684a235732d4320ac26696f2eafc525
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

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