Toluene → HCID 12799916, compound

HRID 2412636Notes

Reaction equation

HRID 2412636 reaction equation
[Br-].[CH3:2][O:3][C:4]([C:6]1[CH:31]=[CH:30][C:9]([CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:8]([NH:32][C:33](=O)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:7]=1)=[O:5].CC(C)([O-])C.[K+].C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl-].[Na+].O>[CH2:34]([C:33]1[NH:32][C:8]2[C:9]([CH:10]=1)=[CH:30][CH:31]=[C:6]([C:4]([O:3][CH3:2])=[O:5])[CH:7]=2)[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 20431900HCID 20431900, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 12799916HCID 12799916, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of [4-methoxycarbonyl-2-(n-dodecanamido)benzyl]triphenylphosphonium bromide (23.8 g) and potassium tert.-butoxide (3.9 g) were added to dry toluene (680 ml). The stirred mixture was heated to reflux for 15 minutes and cooled to room temperature. Ethyl acetate (1.5 liter) and saturated brine (750 ml) were added; the mixture was shaken and the organic phase separated. The organic extract was dried over magnesium sulphate and was evaporated in vacuo to give an oil. The oil was purified by chromatography on a silica column using chloroform as eluant to give a crude solid which was recrystallised from methanol to give methyl 2-(n-undecyl)indole-6-carboxylate (4.1 g) as an off-white solid, m.p. 83°-85° C.

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureto reflux for 15 minutes
  3. customthe organic phase separated
  4. extractionThe organic extract
  5. dry with materialwas dried over magnesium sulphate
  6. customwas evaporated in vacuo
  7. customto give an oil
  8. customThe oil was purified by chromatography on a silica column
  9. customto give a crude solid which
  10. customwas recrystallised from methanol

Sources & evidence

ORD record
ord-6578a46a732743d4b008eec2aa24ab1b
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

Loading…