Phthalimide → HCID 22046405, compound

HRID 1821802Notes

Reaction equation

HRID 1821802 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]O)=[CH:6][C:5]=1[O:12][CH3:13])([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:33]1(=[O:43])[NH:37][C:36](=[O:38])[C:35]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:34]12>C1COCC1>[CH3:13][O:12][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:8][N:37]1[C:33](=[O:43])[C:34]2[C:35](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:36]1=[O:38]

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 6029613-Methoxy-4-nitrobenzyl alcohol

Product 1

HCID 22046405HCID 22046405, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 250 mL round bottomed flask containing 10 g (55 mmol) of 4-nitro-3-methoxybenzyl alcohol in 150 mL THF was added, diethylazodiacarboxylate (8.03 g, 54.6 mmol, 1 eq.) and triphenylphosphine (15.0 g, 57.3 mmol) followed by 11.6 g of phthalimide (57.3 mmol) at 0° C. Reaction was then allowed to gradually warm to room temperature over night. A white precipitate formed and was collected by suction filtration. Recrystallization from acetonitrile gave 13.8 g (81%) of the desired product. 1H NMR (400 MHz, d6-DMSO): δ 7.79 (m, 5H), 7.19 (s, 1H), 7.08 (d, J=8.80 Hz, 1H), 4.91 (s, 2H), 3.87 (s, 3H).

Workup

  1. additionwas added
  2. customReaction
  3. customA white precipitate formed
  4. filtrationwas collected by suction filtration
  5. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-0c0d9f3737924d6ab1b9c6fc35291953
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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