Water → HCID 14664731, compound

HRID 2390897Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].O1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.O.[CH3:14][CH2:15][CH2:16][CH2:17][CH2:18]CC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:8][CH:9]1[C:18]2[C:12](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:11][O:10]1

Participants

Conditions

Temperature: 135 °C

Procedure

The mixture of sodium 1-(2-bromo-phenyl)-ethoxymethyl trifluoroborate (30 mg, 0.092 mmol) synthesized in Example 20, tetrakis(triphenylphosphine)palladium(0) (13 mg, 0.018 mmol), cesium carbonate (90 mg, 0.28 mmol), 1,4-dioxane (1.0 ml), and water (0.10 ml) was stirred at 135° C. for 90 minutes under microwave irradiation. The reaction mixture was cooled to room temperature, and then water and heptane were added thereto, followed by filtration with Celite. The organic layer of the filtrate was separated and washed with saturated saline. The solvents were evaporated under reduced pressure from the organic layer, and then the obtained residue was purified with silica gel column chromatography (hexane alone→hexane:diethyl ether=30:1), thereby obtaining the entitled compound (35.7 mg, 41%).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfollowed by filtration with Celite
customThe organic layer of the filtrate was separated
washwashed with saturated saline
customThe solvents were evaporated under reduced pressure from the organic layer
customthe obtained residue was purified with silica gel column chromatography (hexane alone→hexane

Sources & evidence

ORD record: ord-20c6d6798ebe40c48d67fa02387f16b8
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273885B2

Reaction notes

Loading…