Diethyl Ether → HCID 19047457, compound

HRID 1451337Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.C([Li])CCC.[O:15]1[C:19]2[CH2:20][CH2:21][CH2:22][C:23](=O)[C:18]=2[CH:17]=[CH:16]1.[Cl-].[NH4+].CC[O:29]CC>CCCCCC>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:23]1[C:18]2[CH:17]=[CH:16][O:15][C:19]=2[CH:20]([OH:29])[CH2:21][CH2:22]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 11.1 g (0.0939 mol) of benzofuran in 150 ml of ether cooled to -20° C. was added a solution of 9.39 ml (0.0939 mol) 10M n-butyllithium in hexane, and the mixture was allowed to warm to 0° C. and stirred for 30 min. The mixture was cooled to -78° C. and 10.6 g (0.078 mol) of 4,5,6,7-tetrahydrobenzofuran-4-one in 20 ml of ether was added dropwise and the mixture was allowed to warm to room temperature, and then stirred for 1 h. To the mixture was added saturated ammonium chloride solution and the resulting mixture was extracted with ethyl acetate (3×100 ml). The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo to afford 19.3 g (97%) of 4,5,6,7-tetrahydro-4-(2-benzofuryl)-benzofuran-7-ol, an oil which crystallized on standing as a yellow solid.

Workup

temperatureThe mixture was cooled to -78° C.
temperatureto warm to room temperature
stirringstirred for 1 h
extractionthe resulting mixture was extracted with ethyl acetate (3×100 ml)
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6c1b418674fd4f7481d947bfc10f5093
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05604224

Reaction notes

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