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Water → 4-(3,6-dihydro-2H-pyran-4-yl)benzonitrile

HRID 1626746
Notes
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Reaction equation

HRID 1626746 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].[O:12]1[CH2:17][CH:16]=[C:15](OS(C(F)(F)F)(=O)=O)[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+].O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO.C1(C)C=CC=CC=1>[O:12]1[CH2:13][CH:14]=[C:15]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:16][CH2:17]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 113567033,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate

Product 1

HCID 666330234-(3,6-dihydro-2H-pyran-4-yl)benzonitrileYield 64%

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 887MethanolSolvent
HCID 1140TolueneSolvent

Procedure

2.2 g (15.1 mmol) of (4-cyanophenyl)boronic acid, 2.5 g (10.8 mmol) of 3,6-dihydro-2H-pyran-4-yltrifluoromethanesulfonate, 373 mg (0.32 mmol) of tetrakis(triphenylphosphine)palladium(0) and 1.59 g (15.1 mmol) of sodium carbonate were heated under reflux in a mixed solvent comprising 4 mL of H2O, 57 mL of toluene, and 17 mL of methanol for 3 hours. After the completion of the reaction, the organic solvent was distilled off under reduced pressure, H2O was added to the residue, and ethyl acetate extraction was performed. Subsequently, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography, thereby giving 1.27 g of 4-(3,6-dihydro-2H-pyran-4-yl)benzonitrile (yield: 64%).

Workup

  1. customAfter the completion of the reaction
  2. distillationthe organic solvent was distilled off under reduced pressure, H2O
  3. additionwas added to the residue, and ethyl acetate extraction
  4. dry with materialSubsequently, the organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained crude product
  7. customwas separated
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-84dc698ec0df48dc914f0e16d896c0d7
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08785473B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes