Potassium Carbonate → HCID 67916683, compound

Reaction equation

Br[CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:8][CH:7]=1.[CH3:22][CH2:23][CH2:24][C:25]1[C:30]([OH:31])=[C:29]([C:32]([CH3:34])=[O:33])[CH:28]=[CH:27][C:26]=1[OH:35].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:32]([C:29]1[CH:28]=[CH:27][C:26]([O:35][CH2:2][CH2:3][CH2:4][S:5][C:6]2[CH:11]=[CH:10][C:9]([C:12](=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:8][CH:7]=2)=[C:25]([CH2:24][CH2:23][CH3:22])[C:30]=1[OH:31])(=[O:33])[CH3:34]

Participants

Procedure

The compound of Step A above, (2.0 g, 5.36 mmoles), 2,4-dihydroxy-3-propylacetophenone (2.08 g, 10.72 mmole) and potassium carbonate (3.0 g, 21.44 mmole) were stirred in methyl ethyl ketone (100 ml) and heated at reflux for three hours. The reaction mixture was filtered and concentrated in vacuo. The residue was dissolved in ether-methanol and extracted with 1N NaOH (3×50 ml). The organics were dried and concentrated in vacuo. The residue was triturated with methanol, filtered and dried, to yield the title compound. NMR (CDCl3): 0.94 (3H, m), 1.73 (6H, m), 2.28 (6H, m), 2.95 (2H, m), 3.22 (2H, m), 3.66 (3H, s), 4.17 (2H, m), 6.42 (1H, d), 7.40 (2M, d), 7.61 (1H, d), 7.90 (2H, d), 12.73 (1H, s).