Methyl iodide → HCID 58609940, compound

HRID 408504Notes

Reaction equation

HRID 408504 reaction equation
IC.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2([C:16]([OH:18])=[O:17])[CH2:15][CH2:14]2)=[CH:7][CH:6]=1.[CH:19]1(C#CC2C=CC(OC)=CC=2C(O)=O)CC1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOCC>[CH3:19][O:17][C:16]([C:13]1([C:12]#[C:11][C:8]2[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:10][CH:9]=2)[CH2:14][CH2:15]1)=[O:18]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58609784HCID 58609784, compoundHCID 58609884HCID 58609884, compound

Product 1

HCID 58609940HCID 58609940, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Iodomethane (3.6 g, 0.026 mol) was slowly added to a mixture of 1-(4-methoxy-phenylethynyl)-cyclopropanecarboxylic acid and 2-cyclopropylethynyl-5-methoxy-benzoic acid (5.0 g) and potassium carbonate (4.8 g, 0.034 mol) in DMF (100 mL). After stirring for 4 hours, the mixture was diluted with ether (200 mL) and washed with water. The ether layer was dried over sodium sulfate, evaporated to dryness, and the residue was purified by column chromatography to yield 1-(4-methoxy-phenylethynyl)-cyclopropanecarboxylic acid methyl ester as a yellow oil (2.2 g). 1H NMR (CDCl3): δ 7.36 (d, J=8.8 Hz, 2H), 6.81 (d, J=8.8 Hz. 2H), 3.79 (s, 3H), 3.76 (s, 3H), 1.62 (m, 2H), 1.41 (m, 2H). 2-cyclopropylethynyl-5-methoxy-benzoic acid methyl ester (1.0 g). 1H NMR (CDCl3): δ 7.89 (d, J=2.4 Hz, 1H), 7.46 (dd, J1=8.4 Hz, J2=2.4 Hz, 1H), 6.8 (d, J=8.4 Hz, 1H), 3.88 (s, 3H), 3.87 (s, 3H), 1.43 (m, 1H), 0.86 (m, 2H), 0.78 (m, 2H).

Workup

  1. washwashed with water
  2. dry with materialThe ether layer was dried over sodium sulfate
  3. customevaporated to dryness
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-313679f04dbb422e950d459dc1d6f88b
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Reaction notes

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