3-Oxocyclobutyl benzoate → HCID 86693090, compound

HRID 575057Notes

Reaction equation

[C:1]([O:9][CH:10]1[CH2:13][C:12](=[O:14])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([Mg]Br)#[CH:16]>O1CCCC1>[C:1]([O:9][CH:10]1[CH2:13][C:12]([C:15]#[CH:16])([OH:14])[CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -76 °C

Procedure

This compound was prepared according to a procedure similar to that described in Procedure A. Into a 25-mL three neck-round bottle flask, was placed a solution of 3-oxocyclobutyl benzoate (380 mg, 2.0 mmol, 1.00 equiv) in tetrahydrofuran (10 mL). Ethynylmagnesium bromide (0.5 M in tetrahydrofuran, 6 mL) was added dropwise, then resulting solution was stirred for 30 min at −76° C. When the mixture was warmed to room temperature in air, quenched by addition of saturated aqueous ammonium chloride (5 mL), the organic layer was washed by brine (10 mL), dried and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:6). This resulted in 300 mg (69%) of 3-ethynyl-3-hydroxycyclobutyl benzoate as a white solid. 1H-NMR: (300 MHz, CDCl3, ppm) δ 8.100-8.000 (m, 1H), 7.610-7.500 (t, 1H), 7.499-7.380 (m, 2H), 5.160-5.040 (m, 1H), 3.150-3.010 (m, 2H), 2.610-2.470 (m, 3H).

Workup

customThis compound was prepared
temperatureWhen the mixture was warmed to room temperature in air
customquenched by addition of saturated aqueous ammonium chloride (5 mL)
washthe organic layer was washed by brine (10 mL)
customdried
concentrationconcentrated under vacuum
customThis resulted in 300 mg (69%) of 3-ethynyl-3-hydroxycyclobutyl benzoate as a white solid

Sources & evidence

ORD record: ord-8d205bf35e964f03bd80d19632154333
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034866B2

Reaction notes

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