Diethyl Ether → HCID 67047667, compound

HRID 606932Notes

Reaction equation

HRID 606932 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[C:8]1([C:14]#[C:15][C:16]2[CH:17]=[N:18][CH:19]=[C:20]([CH:24]=2)[C:21]([OH:23])=[O:22])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(OCC)C>CO>[CH3:1][O:22][C:21](=[O:23])[C:20]1[CH:24]=[C:16]([C:15]#[C:14][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:17]=[N:18][CH:19]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 27792365-(2-Phenyleth-1-Ynyl)Nicotinic Acid

Product 1

HCID 67047667HCID 67047667, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add trimethylsilyl diazomethane (2.25 g, 19.7 mmol) to a cooled suspension of 5-phenylethynyl-nicotinic acid (2.0 g, 8.9 mmol) in 4:1 diethyl ether: methanol (30 mL) at 0° C. Warm to room temperature, stir for 2 h and concentrate. Purify the residue by silica gel chromatography, eluting with 0:100 to 50:50 ethyl acetate:hexanes, to give the title compound as a white solid (1.8 g, 85%).

Workup

  1. customat 0° C
  2. concentrationconcentrate
  3. customPurify the residue by silica gel chromatography
  4. washeluting with 0:100 to 50:50 ethyl acetate

Sources & evidence

ORD record
ord-041586667fbc465abfcbadcb613e7bea
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

Loading…