HCID 22238083, compound → HCID 22238093, compound

HRID 1743387Notes

Reaction equation

HRID 1743387 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[C:5]([CH3:17])[C:6]([CH3:16])=[C:7]([O:11]CC(C)=C)[CH:8]=2)[N:3]1[CH:18]=[O:19]>C(N(CC)C1C=CC=CC=1)C.C(OCC)C>[OH:11][C:7]1[C:8]([CH2:6][C:5]([CH3:17])=[CH2:4])=[C:9]2[C:4](=[C:5]([CH3:17])[C:6]=1[CH3:16])[N:3]([CH:18]=[O:19])[CH:2]([CH3:1])[CH2:10]2

Participants

4

Reactant 1

HCID 22238083HCID 22238083, compound

Product 1

HCID 22238093HCID 22238093, compoundYield 137.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7061N,N-DiethylanilineSolvent

Procedure

A solution of 2,3-dihydro-2,6,7-trimethyl-5-[(2-methyl-2-propenyl)oxy]-1H-indole-1-carbaldehyde (0.59 g, 2.3 mmol) in N,N-diethylaniline (3 mL) was stirred at 200° C. for 4.5 hours under the nitrogen atmosphere. The reaction mixture was dissolved in diethyl ether, washed with 1N hydrochloric acid, water and saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-diisopropyl ether to obtain 0.41 g of the title compound.

Workup

  1. washwashed with 1N hydrochloric acid, water and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-77f338ef10fd4377b99ae318e88d33c2
Source dataset
uspto-grants-2006_03
Patent number
US07008940B1

Reaction notes

Loading…