Triethylamine → N-(Allyloxycarbonyloxy)succinimide

HRID 1590698Notes

Reaction equation

HRID 1590698 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].Cl[C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11].C(N(CC)CC)C>O1CCCC1>[C:10](=[O:11])([O:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8])[O:12][CH2:13][CH:14]=[CH2:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18052Allyl chloroformateHCID 80170N-Hydroxysuccinimide

Product 1

HCID 11788855N-(Allyloxycarbonyloxy)succinimide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of N-hydroxysuccinimide (4.78 g, 0.042 mol) and allyl chloroformate (5.0 g, 4.40 ml, 0.042 mmol) in dry tetrahydrofuran (60 ml) was cooled to 0° C. under nitrogen. A solution of triethylamine (4.2 g, 5.78 ml, 0.042 mol) in tetrahydrofuran (20 ml) was added dropwise over 20 minutes. After completion of the addition, the mixture was stirred at room temperature for 4 hours, and then filtered and concentrated. Ethyl acetate (200 ml) was added and the resulting solution was washed sequentially with water (3×), saturated sodium bicarbonate solution and water (3×). Drying (MgSO4) and removal of the solvent in vacuo gave the title compound as a clear, colourless oil. (D23).

Workup

  1. additionAfter completion of the addition
  2. filtrationfiltered
  3. concentrationconcentrated
  4. additionEthyl acetate (200 ml) was added
  5. washthe resulting solution was washed sequentially with water (3×), saturated sodium bicarbonate solution and water (3×)
  6. customDrying
  7. custom(MgSO4) and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-c3f12d56827a49fa85b6f58d9e391000
Source dataset
uspto-grants-1993_04
Patent number
US05204330

Reaction notes

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