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

HRID 1054886Notes

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-0c5c68c2425549ef94aa163e2d9f1b74
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394285B2

Reaction notes

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