Ammonium Chloride → HCID 89906742, compound

Reaction equation

CO[C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)=[CH:6][C:5]=1[OH:15].[CH:17]1([Mg]Cl)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[NH4+].[Cl-]>C1COCC1>[CH:17]1([C:3]([CH:4]2[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)([OH:16])[C:4]2[CH:9]=[CH:8][C:7]([N:10]3[CH:11]=[CH:12][CH:13]=[CH:14]3)=[CH:6][C:5]=2[OH:15])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

Procedure

To a solution of 217 mg of 2-Hydroxy-4-pyrrol-1-yl-benzoic acid methyl ester in 4 ml of THF, 2 ml of a solution of cyclohexylmagnesium chloride in THF (2 M) was added slowly at room temperature. The reaction mixture was then heated to reflux for 4 h. After cooling to room temperature it was hydrolized with ice. Saturated aqueous NH4Cl was added until the white precipitate was dissolved. The aqueous phase was extracted with ether. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was used in the next reaction step. Yield: 504 mg.