Sodium Carbonate → 3-Hydroxy-5-[(1E)-3-(methyloxy)-1-propen-1-yl]benzaldehyde

HRID 1798451Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH:5]=[O:6].[CH3:11][O:12][CH2:13]/[CH:14]=[CH:15]/B1OC(C)(C)C(C)(C)O1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2](/[CH:15]=[CH:14]/[CH2:13][O:12][CH3:11])[CH:9]=1)[CH:5]=[O:6]

Participants

Conditions

Temperature: 80 °C

Procedure

3-Bromo-5-hydroxybenzaldehyde (1 eq.) from the previous step and 2-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1 eq.) were combined in DMF (0.05 M). To this solution was then added palladium acetate (10 mol %), triphenylphosphine (20 mol %), and sodium carbonate (2 M aqueous solution, 4 eq.). The resulting suspension was heated at 80° C. and stirred for 16 h. The reaction mixture was quenched with 10% aqueous HCl and extracted with ether. The combined organic extracts were washed with water, saturated aqueous NaHCO3 solution, brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 20%→33% EtOAc/Hex) to afford the title compound as a yellow oil.

Workup

customThe reaction mixture was quenched with 10% aqueous HCl
extractionextracted with ether
washThe combined organic extracts were washed with water, saturated aqueous NaHCO3 solution, brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe crude product was purified by flash column chromatography (SiO2, 20%→33% EtOAc/Hex)

Sources & evidence

ORD record: ord-868e02e2a72b4c2da14bf3518314ba50
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343968B2

Reaction notes

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