Dimethylformamide → Ethyl 6-(Benzyloxy)benzofuran-2-carboxylate

HRID 1171187Notes

Reaction equation

CN(C)C=O.[CH2:6]([O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[C:16]([OH:22])[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:28]([O:27][C:25]([C:24]1[O:22][C:16]2[CH:15]=[C:14]([O:13][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:21]=[CH:20][C:17]=2[CH:18]=1)=[O:26])[CH3:29]

Participants

Conditions

Temperature: 125 °C

Procedure

To a N,N-dimethylformamide (200 mL) solution of 4-benzyloxy-2-hydroxybenzaldehyde (18.6 g, 81.4 mmol) were added ethyl bromoacetate (9.94 mL, 89.6 mmol) and potassium carbonate (22.6 g, 163 mmol) at room temperature, which was stirred at 125° C. for 3 hours. To the reaction mixture was added water at room temperature followed by extraction with ethyl acetate. After washing the organic layer with water and sat. NaCl, the organic layer was dried over anhydrous magnesium sulfate and filtered followed by concentrating the filtrate under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=7:3) to obtain the title compound (18.4 g, 76%) as a white solid.

Workup

extractionfollowed by extraction with ethyl acetate
washAfter washing the organic layer with water and sat. NaCl
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationby concentrating the filtrate under a reduced pressure
customThe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=7:3)

Sources & evidence

ORD record: ord-1e22375e243248d0a62db7355bdba730
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829585B2

Reaction notes

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