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

HRID 338540
Notes
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Reaction equation

HRID 338540 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 53258655-bromo-3,4-dihydro-2H-pyranHCID 19096565Water ethanol

Product 1

HCID 866988595-(4-chlorophenyl)-3,4-dihydro-2H-pyranYield 58.8%

Reagents, catalysts & solvents 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 1140TolueneSolvent

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

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes