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

HRID 561818Notes

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 from the previous step (1 eq.) 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% loading), triphenylphosphine (20% loading) and sodium carbonate (2 M aqueous solution, 4 eq.). The resulting suspension was heated at 80° C. for 16 h. The reaction mixture was quenched with 10% aq. HCl and extracted with ether. The combined organic extracts were washed with water, sat. aq. NaHCO3 and brine. Drying over MgSO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a brown tar. Purification by way of column chromatography (SiO2, 4:1 (v/v) Hex:EtOAc→2:1 (v/v) Hex:EtOAc) afforded the title compound as a yellow oil.

Workup

customThe reaction mixture was quenched with 10% aq. HCl
extractionextracted with ether
washThe combined organic extracts were washed with water, sat. aq. NaHCO3 and brine
dry with materialDrying over MgSO4, filtration and concentration of the filtrate in vacuo
customafforded the crude product as a brown tar
customPurification by way of column chromatography (SiO2, 4:1 (v/v)

Sources & evidence

ORD record: ord-5d2d19c3fdf444baa37124c41a25304d
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063105B2

Reaction notes

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