1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(4-bromophenyl)-3,6-dihydro-2H-pyran

HRID 338543Notes

Reaction equation

Br[CH:2]1[CH2:7][CH2:6][O:5][CH:4]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)[CH2:3]1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[Br:14][C:11]1[CH:10]=[CH:9][C:8]([CH:4]2[CH2:3][CH:2]=[CH:7][CH2:6][O:5]2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-bromo-2-(4-bromophenyl)tetrahydro-2H-pyran (320 mg, 1.00 mmol) in toluene (5 mL) was added 1,8-Diazabicyclo[5.4.0]undec-7-ene (304 mg, 2.00 mmol). The mixture was stirred at 100° C. for 16 hours. The mixture was then diluted with ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography to give the title compound (150 mg) which contained some impurity of 4-bromobenzaldehyde. 1H NMR (400 MHz, CDCl3) δ ppm 7.48 (d, 2H) 7.30 (d, 2H) 5.92 (m, 1H) 5.82 (m, 1H) 4.52 (dd, 1H) 4.36 (m, 2H) 2.27 (m, 2H).

Workup

washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-1f52fe4c2de54e5598fbf2eec236d4d6
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889730B2

Reaction notes

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