Water → ethyl 8-[4-(2-butoxyethoxy)phenyl]-3,4-dihydro-2H-1-benzoxocin-4-carboxylate

HRID 1810765Notes

Reaction equation

[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23]CCC(OCC)=O)=[C:17]([CH:31]=O)[CH:16]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[O-][CH2:34][CH3:35].[Na+].O.[C:38](=[O:45])([O:42][CH2:43][CH3:44])OCC>C(O)C>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]3[O:21][CH2:22][CH2:23][CH:35]([C:38]([O:42][CH2:43][CH3:44])=[O:45])[CH:34]=[CH:31][C:17]=3[CH:16]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 5-[[4′-(2-butoxyethoxy)-3-formyl [1,1′-biphenyl]-4-yl]oxy]pentanoate (6.00 g) in diethyl carbonate (60 ml) was added a solution of 20% sodium ethoxide in ethanol (5.55 g). The mixture was stirred at 50° C. for 2 hours under a nitrogen atmosphere. The solution was allowed to cool. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain yellowish oil of ethyl 8-[4-(2-butoxyethoxy)phenyl]-3,4-dihydro-2H-1-benzoxocin-4-carboxylate (527 mg).

Workup

temperatureto cool
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated saline
dry with materialdried over magnesium sulfate
distillationAfter distilling off the solvent under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-e1d1a92eaf314552af20ecc3c5ba84b2
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362058B2

Reaction notes

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