Tetrahydrofuran → HCID 19261350, compound

HRID 1740727Notes

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]1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of cyclopropylmagnesium bromide in dry tetrahydrofuran (prepared from cyclopropylbrornide (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 rml) 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-2e08ab1a1eaf4d15946b66c23462f7de
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05972925

Reaction notes

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