Water → 1-Ethynyl-3-(2-methoxyethoxy)benzene

HRID 1435574Notes

Reaction equation

HRID 1435574 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]#[CH:9])[CH:5]=[CH:6][CH:7]=1.Br[CH2:11][CH2:12][O:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH3:14][O:13][CH2:12][CH2:11][O:1][C:2]1[CH:3]=[C:4]([C:8]#[CH:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 139144m-Ethynylphenol

Product 1

HCID 714077821-Ethynyl-3-(2-methoxyethoxy)benzeneYield 70.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Hydroxyphenylacetylene (237 mg, 2 mmol) was heated with 2-bromoethylmethylether (0.23 mL, 2.4 mmol) and potassium carbonate (322 mg, 2.4 mmol) in acetone (5 mL) to 110° C. in a microwave oven (CEM Discover) for 45 minutes. Water (1 mL) was added to the mixture and the whole was extracted with dichloromethane (2×25 mL). The combined organics were dried over MgSO4, filtered and concentrated in vacuo to afford a brown oil. The oil was purified by column chromatography (SiO2, dichloromethane) to afford 3-(2-methoxyethoxy)phenylacetylene as a colourless oil (247 mg, 70% yield).

Workup

  1. extractionthe whole was extracted with dichloromethane (2×25 mL)
  2. dry with materialThe combined organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto afford a brown oil
  6. customThe oil was purified by column chromatography (SiO2, dichloromethane)

Sources & evidence

ORD record
ord-fee8f36f72094b0bb47ce2b12e8e7cfa
Source dataset
uspto-grants-2009_11
Patent number
US07618964B2

Reaction notes

Loading…