Triethylamine → HCID 14986289, compound

HRID 2108255Notes

Reaction equation

HRID 2108255 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH3:11])[CH:3]=1.[CH2:12]([OH:16])[CH2:13][C:14]#[CH:15].C(N(CC)CC)C>C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:11][O:10][C:4]1[CH:3]=[C:2]([C:15]#[C:14][CH2:13][CH2:12][OH:16])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 135663-Butyn-1-OLHCID 76114Benzene, 4-bromo-1,2-dimethoxy-

Product 1

HCID 14986289HCID 14986289, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 10 g (46 mmol) of 1-bromo-3,4-dimethoxybenzene, 3.4 g (48 mmol) of 3-butyn-1-ol and 8 mL (58 mmol) of triethylamine in 20 mL of methylene chloride was stirred and flushed with argon. To the mixture there was added 0.12 g (0.06 mmol) of cuprous iodide and 0.30 g (0.43 mmol) of bis(triphenylphosphine)palladium dichloride. The reaction mixture was stirred at room temperature for 4 hours and at reflux for 16 hours. After filtration, the filtrate was washed with water, dried and concentrated. The crude product was purified by HPLC using 30% ethyl acetate-toluene to give 3.0 g (32% yield) of 4-(3,4-dimethoxyphenyl)-3-butyn-1-ol.

Workup

  1. customflushed with argon
  2. stirringThe reaction mixture was stirred at room temperature for 4 hours
  3. temperatureat reflux for 16 hours
  4. filtrationAfter filtration
  5. washthe filtrate was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-ef115ce3cffa4e60b5944ecbb4ef5bdf
Source dataset
uspto-grants-1990_06
Patent number
US04937373

Reaction notes

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