Tetrahydrofuran → HCID 19261350, compound

HRID 1291031Notes

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 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-cld 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-2c7db289972f475baa0a1cc628e94603
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05753678

Reaction notes

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