2-Propynoic acid, 3-(4-fluorophenyl)-, methyl ester → HCID 21948679, compound

HRID 2214928Notes

Reaction equation

HRID 2214928 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:27][N+:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34].N1(C2CCCCCCCCCC2)CCCN=CCCCCC1>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:33]3[CH:32]=[CH:31][CH:30]=[C:29]([CH3:34])[N:28]3[N:27]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 111268212-Propynoic acid, 3-(4-fluorophenyl)-, methyl esterHCID 120228721-Amino-2-methylpyridinium 2,4,6-trimethylbenzenesulfonateHCID 1296629601,8-Diazabicycloundec-7ene

Product 1

HCID 21948679HCID 21948679, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of methyl 3-(4-fluorophenyl)propiolate (3.47 g, 19.5 mmol) and 1-amino-2-methylpyridinium 2,4,6-trimethylbenzenesulfonate (6.0 g, 19.5 mmol) in dry acetonitrile (75 mL) was added, dropwise over 10 min a solution of 1,8-diazabicycloundec-7-ene (5.82 mL, 39 mmol) in dry acetonitrile (25 mL). The mixture was allowed to stir at room temperature for about 18 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between water (500 mL) and ethyl acetate (250 mL) and the organic phase separated. The aqueous was extracted with ethyl acetate and the combined organic extracts are dried over anhydrous magnesium sulfate, and the solvent removed under vacuum. The residue was purified by chromatography on silica gel using 10:1 hexanes:ethyl acetate as eluent to give the title compound as a white solid, 4.65 g (86%). 1H NMR (CDCl3) δ 8.15 (d, 1H, J=8.8 Hz), 7.86 (m, 2H), 7.41 (t, 1H, J=8.9 Hz), 7.19 (t, 2H, J=17.6 Hz), 6.87 (d, 1H, J=7.0 Hz), 3.89 (s, 3H), 2.85 (s, 3H). MS (+ve ion electrospray) 285 (100), (MH+).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between water (500 mL) and ethyl acetate (250 mL)
  3. customthe organic phase separated
  4. extractionThe aqueous was extracted with ethyl acetate
  5. dry with materialthe combined organic extracts are dried over anhydrous magnesium sulfate
  6. customthe solvent removed under vacuum
  7. customThe residue was purified by chromatography on silica gel using 10:1 hexanes

Sources & evidence

ORD record
ord-07cec1bfacc44c0f889993482ad172c0
Source dataset
uspto-grants-2006_09
Patent number
US07109209B2

Reaction notes

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