1,4-Dioxane → HCID 12799930, compound

HRID 2412618Notes

Reaction equation

HRID 2412618 reaction equation
[CH2:1]([C:16]1[NH:17][C:18]2[C:23]([C:24]=1C)=[CH:22][C:21]([C:26]([O:28][CH2:29][CH3:30])=S)=[CH:20][CH:19]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[O:31]1CCOCC1>[Ni]>[CH2:1]([C:16]1[NH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][C:21]([C:26]([O:28][CH2:29][CH3:30])=[O:31])=[CH:20][CH:19]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 86739871HCID 86739871, compound

Product 1

HCID 12799930HCID 12799930, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Raney nickel (5 g) was added to a solution of ethyl 2-(n-pentadecyl)-3-methylthioindole-5-carboxylate (0.5 g) in dioxan (25 ml) and the mixture was heated on a steam bath for 1 hour. The mixture was filtered hot and the filtrate was evaporated in vacuo to give a white solid. This solid was recrystallised from petroleum ether (b.p. 60°-80° C.) to give ethyl 2-(n-pentadecyl)indole-5-carboxylate (0.35 g), m.p. 89°-91° C.

Workup

  1. temperaturethe mixture was heated on a steam bath for 1 hour
  2. filtrationThe mixture was filtered hot
  3. customthe filtrate was evaporated in vacuo
  4. customto give a white solid
  5. customThis solid was recrystallised from petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-448f5cbeb7d74ccc8400d3158a8bb824
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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