Propargyl bromide → Methyl (4'-methoxy-3'-(2-propynyloxy)biphenyl-3-yl)acetate

HRID 2247444Notes

Reaction equation

HRID 2247444 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH2:21](Br)[C:22]#[CH:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:11]=2)=[CH:3][C:2]=1[O:1][CH2:23][C:22]#[CH:21]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 59219199Methyl (3'-hydroxy-4'-methoxybiphenyl-3-yl)acetate

Product 1

HCID 59218932Methyl (4'-methoxy-3'-(2-propynyloxy)biphenyl-3-yl)acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

207 mg methyl (3′-hydroxy-4′-methoxybiphenyl-3-yl)acetate was dissolved in 3 ml N,N-dimethylformamide, 0.17 ml propargyl bromide and 150 mg potassium carbonate were added thereto, and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate and washed with 1 N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography, to give 221 mg of the title compound in the 4:1 hexane-ethyl acetate fraction.

Workup

  1. washwashed with 1 N hydrochloric acid
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-aecab0473cdc4b6987f42fbda814bc2d
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

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