Acetyl chloride → HCID 66914882, compound

HRID 880462Notes

Reaction equation

HRID 880462 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[N:10]([CH2:20][CH2:21][OH:22])[CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=1.[C:23](Cl)(=[O:25])[CH3:24]>ClCCl>[C:23]([O:22][CH2:21][CH2:20][N:10]1[CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=[C:9]1[CH3:8])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 66914765HCID 66914765, compound

Product 1

HCID 66914882HCID 66914882, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.5 mL, 3.59 mmol) was added dropwise to a solution of 2-(2-methyl-4-phenyl-pyrrol-1-yl)ethanol (260 mg, 1.29 mmol) in dry dichloromethane (20 mL) at 0 to 5° C. followed by the addition of acetyl chloride (0.2 mL, 2.81 mmol). The reaction mixture was stirred for 30 min and then quenched into ice water (30 mL) and ethyl acetate (20 mL) and stirred for 15 min. The organic layer was separated and washed with water (2×25 mL), brine (2×25 mL), dried over anhydrous sodium sulphate and concentrated in vacuo to afford 2-(2-methyl-4-phenyl-pyrrol-1-yl)ethyl acetate (300 mg, 96%) as a brown liquid.

Workup

  1. customquenched into ice water (30 mL) and ethyl acetate (20 mL)
  2. stirringstirred for 15 min
  3. customThe organic layer was separated
  4. washwashed with water (2×25 mL), brine (2×25 mL)
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26ef9ec586ec43909631f5b19efbe53d
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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