Trimethylamine → HCID 71478173, compound

HRID 527169Notes

Reaction equation

HRID 527169 reaction equation
[OH:1][C:2]12[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:14])[C:6]1([NH:15][C:16](=[O:18])[CH3:17])[C:5]1[CH:19]=[CH:20][C:21]([CH:23]([CH3:25])[CH3:24])=[CH:22][C:4]=1[O:3]2.CN(C)C>C1COCC1>[C:16]([N:15]([C:6]1([C:5]2[CH:19]=[CH:20][C:21]([CH:23]([CH3:24])[CH3:25])=[CH:22][C:4]=2[OH:3])[C:2](=[O:1])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:14])[C:2](=[O:1])[O:3][CH2:4][CH3:5])(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 1146TrimethylamineHCID 86716885HCID 86716885, compound

Product 1

HCID 71478173HCID 71478173, compoundYield 151%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4b-hydroxy-7-isopropyl-10-oxo-4b,10-dihydro-9bH-indeno[1,2-b]benzofuran-9b-yl)acetamide (0.70 g, 2.07 mmol) was dissolved in anhydrous THF (15 ml). This solution was added with Ethyl chroloformate (0.32 g, 3.11 mmol) and Trimethylamine (0.25 g, 2.48 mmol). The reaction mixture was stirred for 4 hrs. After concentrating in a vacuum to remove THF, and the remainder was diluted with Methylene chrolide and washed with water many times. After drying and filtrating, the organic layer was purified using column chromatography (ethylacetate:hexane=1:4) to afford the title compound (0.64 g, 71%).

Workup

  1. concentrationAfter concentrating in a vacuum
  2. customto remove THF
  3. additionthe remainder was diluted with Methylene chrolide
  4. washwashed with water many times
  5. customAfter drying
  6. filtrationfiltrating
  7. customthe organic layer was purified

Sources & evidence

ORD record
ord-97ceb9ab42b846d0a97ee04208efbc1e
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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