Epichlorohydrin → (1-methyl-1H-indol-4-yl) [2-(2-oxiranylmethoxy)-phenyl]methanone

HRID 1533992Notes

Reaction equation

HRID 1533992 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[CH:13][N:14]2[CH3:19])=[O:9].C(=O)([O-])[O-].[K+].[K+].[CH2:26]([CH:28]1[O:30][CH2:29]1)Cl>>[CH3:19][N:14]1[C:15]2[C:11](=[C:10]([C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[O:1][CH2:26][CH:28]3[CH2:29][O:30]3)=[O:9])[CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:13]1

Participants

4

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 67854425(2-hydroxyphenyl)-(1-methyl-1H-indol-4-yl) methanone

Product 1

HCID 88465110(1-methyl-1H-indol-4-yl) [2-(2-oxiranylmethoxy)-phenyl]methanone

Procedure

Using the procedure of Step A of Example 3, 3 g of the product of Step D, 6.6 g of potassium carbonate and 4.7 ml of epichlorhydrin were added in 5 stages. After a total of 48 hours at reflux, filtration was carried out. The filtrate was concentrated to dryness under reduced pressure and the residue was chromatographed as indicated in Example 2 to obtain 3.7 g of the expected product.

Workup

  1. additionwere added in 5 stages
  2. temperatureAfter a total of 48 hours at reflux
  3. filtrationfiltration
  4. concentrationThe filtrate was concentrated to dryness under reduced pressure
  5. customthe residue was chromatographed

Sources & evidence

ORD record
ord-41c27a5a85c049388b57ffbf7392fe94
Source dataset
uspto-grants-1992_02
Patent number
US05086070

Reaction notes

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