Picolyl chloride hydrochloride → HCID 22241408, compound

HRID 892196Notes

Reaction equation

HRID 892196 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[CH:12][CH:13]=1.[H-].[Na+].Cl.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25]Cl.CN1C(=O)N(C)CCC1>C1COCC1.CCOC(C)=O>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[CH2:14][O:15][CH2:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=1

Participants

7

Reactant 4

HCID 23392Picolyl chloride hydrochlorideHCID 24758Sodium hydrideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 22241324HCID 22241324, compound

Product 1

HCID 22241408HCID 22241408, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cooled solution (0° C.) of [3-(2-methoxy-ethoxymethoxy)-phenyl]-methanol (212 mg, 1 mmol, example 72) in THF (3 mL) is added 60% NaH (80 mg, 2 mmol) and the mixture stirred 10 min. Added 2-picolyl chloride hydrochloride (164 mg, 1 mmol) and DMPU (0.8 mL), removed cold bath and let reaction mixture stir for 2 hrs. Quenched reaction with sat NH4Cl soln. and diluted with EtOAc. The organic layer is washed with brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (silica, 70% ethyl acetate in hexanes) to give the title compound as a pale yellow oil. MS (ESI) 304 (M+H)+.

Workup

  1. customreaction mixture
  2. stirringstir for 2 hrs
  3. customQuenched
  4. customreaction with sat NH4Cl soln
  5. washThe organic layer is washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue is purified by flash chromatography (silica, 70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ddd5c3196a5340db9bac3210f88bd577
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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