Isopropanol → 2-(1-Methylethoxy)-1H-isoindole-1,3(2H)-dione

HRID 1752126Notes

Reaction equation

HRID 1752126 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH3:13][CH:14]([OH:16])[CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:37]1[C:41](=[O:42])[C:40]2=[CH:43][CH:44]=[CH:45][CH:46]=[C:39]2[C:38]1=[O:47]>C1COCC1>[CH:14]([O:16][N:37]1[C:41](=[O:42])[C:40]2[C:39](=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:38]1=[O:47])([CH3:15])[CH3:13]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 27689132-(1-Methylethoxy)-1H-isoindole-1,3(2H)-dioneYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (14.5 mL, 73.56 mmol) was added dropwise at 0° C. to a stirred suspension of propan-2-ol (4.7 mL, 61.30 mmol), triphenylphosphine (19.30 g, 73.56 mmol), and N-hydroxyphthalimide (10.00 g, 61.30 mmol) in THF (50 mL). The mixture was stirred at room temperature for 20 h and evaporated to dryness. The product was purified by flash column chromatography using gradient elution from petroleum ether/EtOAc (9:1) to petroleum ether/EtOAc (5:1) to yield 2-isopropoxy-isoindole-1,3-dione (LIX, 10.92 g, 87%). 400 MHz 1H NMR (DMSO-d6, ppm): 7.86 (4H, s), 4.44 (1H, septet, J=6.2 Hz), 1.28 (6H, d, J=6.2 Hz).

Workup

  1. customevaporated to dryness
  2. customThe product was purified by flash column chromatography
  3. washelution from petroleum ether/EtOAc (9:1) to petroleum ether/EtOAc (5:1)

Sources & evidence

ORD record
ord-a6af9e4dede24d4a97983c3d82699252
Source dataset
uspto-grants-2015_10
Patent number
US09162992B2

Reaction notes

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