Ethylene carbonate → HCID 22036444, compound

HRID 991650Notes

Reaction equation

HRID 991650 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].C1(=O)O[CH2:20][CH2:19][O:18]1>CN(C=O)C>[NH:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([O:1][CH2:20][CH2:19][OH:18])[CH:10]=2)[CH:6]=[CH:7]1

Participants

5

Reactant 3

HCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 5245086-Hydroxyindole

Product 1

HCID 22036444HCID 22036444, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
125 °C

Procedure

A mixture of 6-hydroxyindole (2.66 g, 20 mmol) and K2CO3 (3.04 g, 22 mmol) was stirred in DMF (10 mL) at 80° C. for 10 min. A solution of ethylene carbonate (1.94 g, 22 mmol) in DMF (4 mL) was added and the mixture was heated at 125° C. for 3 h. The mixture was concentrated, diluted with water, and extracted with toluene. The organic phase was washed with 1 M aqueous Na2CO3 and brine. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash chromatography on silica using EtOAc/toluene (1:4→36:65) as eluent. Yield 1.02 g (29%); mp 74-77° C.; HRMS m/z calcd for C10H11NO2 (M)+ 177.0790, found 177.0784. Anal. (C10H11INO2) C, H, N.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with toluene
  4. washThe organic phase was washed with 1 M aqueous Na2CO3 and brine
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-d5f4105a8e5e4b249e355989b5e2c8f5
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Reaction notes

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