Ethyl Acetate → HCID 57443484, compound

HRID 546834Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[O:6][C:7](Br)=[CH:8][CH:9]=1)=[O:4].C(=O)([O-])[O-].[Na+].[Na+].[CH2:17]([C:19]([C:38]1[CH:43]=[CH:42][C:41]([OH:44])=[C:40]([CH3:45])[CH:39]=1)([C:22]1[CH:27]=[CH:26][C:25](B2OC(C)(C)C(C)(C)O2)=[C:24]([CH3:37])[CH:23]=1)[CH2:20][CH3:21])[CH3:18].C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([C:25]2[CH:26]=[CH:27][C:22]([C:19]([CH2:20][CH3:21])([C:38]3[CH:43]=[CH:42][C:41]([OH:44])=[C:40]([CH3:45])[CH:39]=3)[CH2:17][CH3:18])=[CH:23][C:24]=2[CH3:37])=[CH:8][CH:9]=1)=[O:4]

Participants

Conditions

Temperature: 85 °C

Procedure

5-Bromo-furan-2-carboxylic acid methyl ester (J. Org. Chem., 1988, 53(9), 2099.; 156 mg, 0.761 mmol), tetrakistriphenylphosphine palladium (15 mg, 0.013 mmol) and a 2 M sodium carbonate aqueous solution (0.3 mL, 0.6 mmol) were added to a solution of 4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenol (Example 15-(2); 100 mg, 0.254 mmol) in toluene (0.5 mL) at room temperature, and the mixture was stirred at 85° C. for 17 hours. Ethyl acetate was added to the reaction solution. The organic layer was filtered through celite, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=3/1) to give the title compound (73.6 mg, 73.9%).

Workup

filtrationThe organic layer was filtered through celite
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel chromatography (n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record: ord-17745f86694140fba6cd1dd396d317c0
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935688B2

Reaction notes

Loading…