Acetyl chloride → HCID 10539326, compound

HRID 21598Notes

Reaction equation

HRID 21598 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5]2.[C:17](Cl)(=[O:19])[CH3:18].C(N(CC)CC)C>O1CCCC1.O>[C:17]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5]2)(=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 15365972Ethyl 5-hydroxy-1-methyl-1H-indole-2-carboxylate

Product 1

HCID 10539326HCID 10539326, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 5-hydroxy-1-methyl-1H-indole-2-carboxylate (2.2 g, 10.0 mmol) in 50 mL of tetrahydrofuran is treated dropwise with acetyl chloride (0.80 mL, 0.88 g, 11.3 mmol) followed by triethylamine (1.6 mL, 1.2 g, 11.5 mmol). The mixture is stirred at room temperature for 16 hours, then diluted with water and extracted with ethyl acetate. The combined organic layers are washed with brine, dried (anhydrous magnesium sulfate), and evaporated. Recrystallization of the residue from ether-pentane gives 2.0 g (77%) of product; mp 87°-89° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. customevaporated
  5. customRecrystallization of the residue from ether-pentane

Sources & evidence

ORD record
ord-14aef013f159495ea52609d00748cb42
Source dataset
uspto-grants-1995_06
Patent number
US05424329

Reaction notes

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