Sodium Carbonate → 4-(Benzyloxy)-2-(chloromethyl)pyridine

HRID 472898Notes

Reaction equation

HRID 472898 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([CH2:19]O)[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([CH2:19][Cl:3])[CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 105606244-(Phenylmethoxy)-2-pyridinemethanol

Product 1

HCID 129385594-(Benzyloxy)-2-(chloromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.76 ml (24.16 mmol) of thionyl chloride are added to 2 g (9.29 mmol) of [4-(benzyloxy)pyridin-2-yl]methanol [described in J. Org. Chem., (1996), 61(8), 2624] in 46 ml of dichloromethane. The reaction medium is stirred at ambient temperature for 18 hours and then concentrated under reduced pressure. The residue obtained is taken up in a saturated aqueous sodium carbonate solution and then extracted with dichloromethane. The organic phase is dried over sodium sulfate and then concentrated under reduced pressure. 2.1 g of a brown oil are collected. Mass spectrometry (ES+Mode): MH+=234

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. custom2.1 g of a brown oil are collected

Sources & evidence

ORD record
ord-a4880af9adaa44e3847fcbb7591d7f4c
Source dataset
uspto-grants-2014_01
Patent number
US08633216B2

Reaction notes

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