Methallyl alcohol → 343319-60-8

HRID 1912749Notes

Reaction equation

HRID 1912749 reaction equation
[CH3:1][C:2](=[CH2:5])[CH2:3][OH:4].O[N:7]1[C:11](=[O:12])[C:10]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]2[C:8]1=[O:17].N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:5][C:2](=[CH2:1])[CH2:3][O:4][N:7]1[C:11](=[O:12])[C:10]2[C:9](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]1=[O:17]

Participants

5

Reactant 3

HCID 10557Methallyl alcoholHCID 10665N-HydroxyphthalimideHCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 12498584343319-60-8Yield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methyl-2-propen-1-ol (0.856 g) triphenyl phosphine (4.67 g) and N-hydroxyphthalimide (2.90 g) in THF (90 mL), at 0° C., diisopropyl azodicarboxylate (3.51 mL) was added. After stirring for 2 hours, the solvent was evaporated and the crude product was purified by flash chromatography (SiO2, cyclohexane/EtOAc 85/15) to give 2-(2-methylallyloxy)isoindole-1,3-dione (2.13 g, 83%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 7.80 (4H, bs), 5.02 (2H, d), 4.54 (2H, s), 1.83 (3H, s).

Workup

  1. customthe solvent was evaporated
  2. customthe crude product was purified by flash chromatography (SiO2, cyclohexane/EtOAc 85/15)

Sources & evidence

ORD record
ord-9428340e08804678a587135be7e5993d
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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