Hydrochloric Acid → HCID 67211750, compound

HRID 1401882Notes

Reaction equation

[C:1]([CH:5]1[CH2:10][CH2:9][C:8](B(O)O)=[CH:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH2:14]([OH:16])[CH3:15].[C:17](=[O:20])([O-])[O-].[Na+].[Na+].Cl>C1COCC1.O>[CH2:14]([O:16][C:17](=[O:20])[CH2:1][C:5]1[CH:10]=[CH:9][C:8]([C:8]2[CH2:9][CH2:10][CH:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:6][CH:7]=2)=[CH:7][CH:6]=1)[CH3:15]

Participants

Conditions

Temperature: 140 °C

Procedure

To a mixture of 4-bromophenyl ethyl acetate (780 mg), 4-t-butyl-cyclohexen-1-yl boronic acid (897 mg), PdCl2(P(o-tolyl)3)2 (254 mg) in THF:ethanol:water (8 mL:4 mL:2 mL), added sodium carbonate (1.377 g). The sealed flask was heated at 140° C. for a 5 min period. The heterogeneous mixture was treated with an excess of 1M aqueous hydrochloric acid and filtered through a celite pad. The organic solvents were removed under reduced pressure and the residue partitioned between ethyl acetate and water. The organic phase was washed with water and saturated aqueous sodium chloride, dried over magnesium sulfate and chromatographed on silica gel using an ethyl acetate/hexanes gradient. The product was obtained as a yellow oil.

Workup

filtrationfiltered through a celite pad
customThe organic solvents were removed under reduced pressure
customthe residue partitioned between ethyl acetate and water
washThe organic phase was washed with water and saturated aqueous sodium chloride
dry with materialdried over magnesium sulfate
customchromatographed on silica gel using an ethyl acetate/hexanes gradient
customThe product was obtained as a yellow oil

Sources & evidence

ORD record: ord-32f8a89f8e144460958acf707c66d1f8
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907103B2

Reaction notes

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