Tetrahydrofuran → HCID 19261350, compound
Reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.C1(Br)CC1.[Mg].[CH2:11]1[C:22]2[CH2:21][C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[O:18][CH2:17][O:16][C:15]=2[CH:14]=[CH:13][C:12]1=O.[Cl-].[NH4+].[O:30]1CCCC1>CCOCC>[CH:1]1([C:21]2([OH:30])[C:22]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[O:16][CH2:17][O:18][C:19]3[CH:26]=[CH:25][CH:24]=[CH:23][C:20]2=3)[CH2:3][CH2:2]1Participants
Conditions
- Temperature
- 40 °C
Procedure
A solution of cyclopropylmagnesium bromide in dry tetrahydrofuran (prepared from cyclopropylbromide (24.2 g, 0.2 mol), magnesium turnings (4.86 g, 0.2 mol) and dry tetrahydrofuran (70 ml) was placed under an atmosphere of nitrogen. A solution of the above ketone (9.05 g, 40 mmol) in dry tetrahydrofuran (50 ml) was added dropwise. The reaction mixture was stirred at 40° C. for 1.5 h, cooled and added to an ice-cold mixture of saturated ammonium chloride (400 ml) and ether (200 ml). The organic layer was separated, the aqueous phase was extracted with ether (50 ml), the combined organic extracts were washed with water (2×100 ml) and brine (50 ml), dried over MgSO4, evaporated in vacuo and stripped with toluene (2×25 ml) to furnish 11.2 g 12-cyclopropyl-12H-dibenzo[d,g][1,3]dioxocin-12-ol.
Workup
- temperaturecooled
- customThe organic layer was separated
- extractionthe aqueous phase was extracted with ether (50 ml)
- washthe combined organic extracts were washed with water (2×100 ml) and brine (50 ml)
- dry with materialdried over MgSO4
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-0d146f41aca340e8abeac268c97e1e9d
- Source dataset
- uspto-grants-1999_06
- Patent number
- US05917047
Reaction notes
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