Potassium Carbonate → 5-(4-chlorophenyl)-3,4-dihydro-2H-pyran

HRID 338540Notes

Reaction equation

Br[C:2]1[CH2:3][CH2:4][CH2:5][O:6][CH:7]=1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C.O>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:2]2[CH2:3][CH2:4][CH2:5][O:6][CH:7]=2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-bromo-3,4-dihydro-2H-pyran (1.0 g, 6.13 mmol), (4-chlorophenyl)boronic acid (1.05 g, 6.74 mmol), potassium carbonate (2.5 g, 18.4 mmol), Pd(dppf)Cl2 (449 mg, 0.613 mmol), and ethanol/water (2/2 mL) in toluene (10 mL) was stirred at 100° C. for 12 hours. The mixture was filtered, and the filtrate was evaporated and purified by silica gel chromatography to give the title compound (700 mg, 58.8%) as orange solid. 1H NMR (400 MHz, CD3OD) δ ppm 7.25 (d, 2H), 7.20 (d, 2H) 6.90 (s, 1H), 4.03 (t, 2H), 2.37 (t, 2H), 2.02 (m, 2H)

Workup

filtrationThe mixture was filtered
customthe filtrate was evaporated
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-413b92b2dc0943a2ae26205ad8f8e95b
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889730B2

Reaction notes

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