Methanol → Methyl alpha-Benzylindole-3-acetate

HRID 621720Notes

Reaction equation

HRID 621720 reaction equation
[CH2:1]([CH:8]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:26]O>>[CH2:1]([CH:8]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)[C:9]([O:11][CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 12227608HCID 12227608, compound

Product 1

HCID 14064717Methyl alpha-Benzylindole-3-acetate

Procedure

To a solution of α-benzylindole-3-acetic acid (12 g) in methanol (200 mL), was added 2 mL of concentrated H2SO4 ; the mixture was stirred at reflux temperature for 2 hours. The reaction mixture was concentrated under reduced pressure to a volume of about 50 mL, then diluted with 200 mL of toluene. The toluene solution was washed with water, saturated NaHCO3 solution, and again with water. On evaporation, if afforded 12.3 g (97.6% crude yield) of product as a light brown viscous oil. The crude product slowly crystallized on standing at room temperature. It was triturated with heptane to give fine white crystals, m.p. 62°-68° C.

Workup

  1. temperatureat reflux temperature for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure to a volume of about 50 mL
  3. additiondiluted with 200 mL of toluene
  4. washThe toluene solution was washed with water, saturated NaHCO3 solution
  5. customOn evaporation
  6. customif afforded 12.3 g (97.6% crude yield) of product as a light brown viscous oil
  7. customThe crude product slowly crystallized
  8. customon standing at room temperature
  9. customIt was triturated with heptane
  10. customto give fine white crystals, m.p. 62°-68° C.

Sources & evidence

ORD record
ord-bd1a9f9896e44e4badc8c885fc77464f
Source dataset
uspto-grants-1989_04
Patent number
US04824961

Reaction notes

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