Water → HCID 17952721, compound

HRID 1394575Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[C:14]([CH2:16][CH3:17])[CH:13]=[C:12]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:11]=2[O:22][CH2:23][O:24][CH3:25])=[CH:6][C:3]=1[CH:4]=O.Cl[CH2:27][C:28](=[O:30])[CH3:29].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[C:28]([C:27]1[O:1][C:2]2[CH:9]=[CH:8][C:7]([C:10]3[CH:15]=[C:14]([CH2:16][CH3:17])[CH:13]=[C:12]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:11]=3[O:22][CH2:23][O:24][CH3:25])=[CH:6][C:3]=2[CH:4]=1)(=[O:30])[CH3:29]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 333 mg (0.969 mmol) of 2-hydroxy-5-(5-ethyl-3-tert-butyl-2-methoxymethoxyphenyl)-benzaldehyde, 116 mg (1.26 mmol, 0.1 mL) of chloroacetone and 473 mg (1.45 mmol, 1.5 equivalents) of Cs2CO3 in 5 mL of dry DMF was heated to 60° C. overnight. After cooling, water was added (15 mL) and the solution was extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over MgSO4. Evaporation of the solvents followed by purification over a short silica plug afforded 2-acetyl-5-(5-ethyl-3-tert-butyl-2-methoxymethoxyphenyl)-benzo[b]furan as a clear yellow oil (200 mg, 0526 mmol, yield: 54%). 1H NMR(CDCl3), δ:7.85 (d, J=1.4 Hz, 1H), 7.68 (dd, J=8.7, 1.7 Hz, 1H), 7.62 (d, J=8.7 Hz, 1H), 7.19 (d, J=2.1 Hz, 1H), 7.02 (d, J=2.3 Hz, 1H), 4.44 (s, 2H), 3.21 (s, 3H), 2.65 (m, 2H), 2.63 (s, 3H), 1.48 (s, 9H), 1.27 (t, J=7.7 Hz, 3H).

Workup

temperatureAfter cooling
extractionthe solution was extracted with ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried over MgSO4
customEvaporation of the solvents
customfollowed by purification over a short silica plug

Sources & evidence

ORD record: ord-19fbd634446c46fcbbf95dd9123109b6
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348359B2

Reaction notes

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