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

HRID 1947470Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11]([OH:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:24]([O:26][C:27](=[O:30])[CH2:28]Br)[CH3:25].O>CN(C=O)C>[CH2:24]([O:26][C:27]([C:28]1[O:17][C:11]2[CH:10]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:16]=[CH:15][C:12]=2[CH:13]=1)=[O:30])[CH3:25]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-benzyloxy-2-hydroxy-benzaldehyde (10.0 g, 44 mmol) in DMF (400 mL) is added K2CO3 (18.6 g, 131 mmol) followed by bromo-acetic acid ethyl ester (5.4 mL, 8.1 g, 48 mmol) and the resulting mixture was heated (80° C., 12 h). The reaction mixture was cooled (rt) and treated with H2O (200 mL). The solid was filtered to afforded the title compound as a beige solid (8.1 g, 62%). MS (ESI): mass calcd. for C18H16O4, 296.1; m/z found, 297.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.53 (d, J=8.7, 1H), 7.48-7.30 (m, 6H), 7.12 (d, J=2.0, 1H), 7.01 (dt, J=6.1, 3.1, 1H), 5.09 (d, J=28.6, 2H), 4.42 (q, J=7.1, 2H), 1.37 (dt, J=36.6, 9.6, 3H).

Workup

temperatureThe reaction mixture was cooled (rt)
filtrationThe solid was filtered

Sources & evidence

ORD record: ord-72a5d00265b74333826ab1dd105396db
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399465B2

Reaction notes

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