Toluene → HCID 63220265, compound

HRID 1186353Notes

Reaction equation

HRID 1186353 reaction equation
C1(C)C=CC=CC=1.C([Li])CCC.Br[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.[O:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1>CCCCCC.O1CCCC1>[OH:26][C:23]1([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH2:24][CH2:25][O:20][CH2:21][CH2:22]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 122863-BromopyridineHCID 121599Tetrahydro-4H-pyran-4-oneHCID 178418339Butyllithium

Product 1

HCID 63220265HCID 63220265, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

According to Reference Example 8-23, by use of toluene (3.3+1.1 mL), n-butyllithium (a 2.77 mol/L solution in hexane, 1.24 mL, 2.28 mmol), 3-bromopyridine (300 μL, 3.12 mmol), tetrahydrofuran (1.1 mL) and tetrahydropyran-4-one (345 μL, 3.74 mmol), the mixture was stirred and reacted at 0° C. for 2 hours. Then, purification by silica gel column chromatography (chloroform/methanol=19/1) was performed to give 4-hydroxy-4-(pyridin-3-yl)tetrahydropyran (Compound DF) (167 mg, yield: 30%).

Workup

  1. customreacted at 0° C. for 2 hours
  2. customThen, purification by silica gel column chromatography (chloroform/methanol=19/1)

Sources & evidence

ORD record
ord-47176577def84615831e8c648cfd3cc2
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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