Potassium Carbonate → HCID 86595578, compound

HRID 402255Notes

Reaction equation

Br[C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([CH:18]=[O:19])[CH:3]=1.[CH2:20]([O:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31](OB(O)O)=[CH:30][CH:29]=1)[CH2:21][CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O>[CH2:20]([O:24][CH2:25][CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([C:2]2[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([CH:18]=[O:19])[CH:3]=2)=[CH:32][CH:33]=1)[CH2:21][CH2:22][CH3:23]

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of ethyl 5-(4-bromo-2-formylphenoxy)pentanoate (9.0 g) and 4-(2-butoxyethoxy)phenylboric acid (7.8 g) and potassium carbonate (9.1 g) in toluene (100 ml), ethanol (10 ml) and water (10 ml) was stirred under an argon atmosphere for 30 minutes. After addition of tetrakis(triphenyl)phosphine palladium (1.6 g), the solution was heated at 100° C. for 12 hours under an argon atmosphere. The solution was allowed to cool. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain brown amorphous ethyl 5-[[4′-(2-butoxyethoxy)-3-formyl[1,1′-biphenyl]-4-yl]oxy]pentanoate (12.0 g).

Workup

temperatureto cool
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated saline
dry with materialdried over magnesium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-32cc26cce184476f8ceedba3b1a6780c
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741943B2

Reaction notes

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