Hydrochloric Acid → HCID 23159879, compound

HRID 2110839Notes

Reaction equation

HRID 2110839 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[C:13]2[CH3:21])[CH:9]=[CH:10][CH:11]=1.Cl.O>O1CCCC1>[CH3:21][C:13]1[N:12]([C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=2)[CH:2]=[O:1])[C:20]2[C:15]([CH:14]=1)=[CH:16][CH:17]=[CH:18][CH:19]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 23159936HCID 23159936, compound

Product 1

HCID 23159879HCID 23159879, compoundYield 5.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

1-[3-(1,3-Dioxolan-2-yl)phenyl]-2-methyl-1H-indole (1.1 g, 3.94 mmol) synthesized according to the method described in J. Am. Chem. Soc., 2002, vol. 124, pp. 11684-11688 was dissolved in tetrahydrofuran (40 mL), 5 N hydrochloric acid (10 mL) was added to the solution, and the mixture was stirred at 50° C. for 40 min. Water was added to the reaction solution and the mixture was extracted with ethyl acetate. The extract was washed with aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:6) to give the title compound (50 mg, yield 5%) as a pale-yellow oil. MS: m/z 236 (MH+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4c6cd27c23474069a1f138901a81dfc2
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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