Water → 5-(Benzyloxy)-2-tert-butylpyridine

HRID 63277

Reaction equation

HRID 63277 reaction equation
[Cu]C#N.[C:4]([Mg]Cl)([CH3:7])([CH3:6])[CH3:5].Br[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][N:12]=1.O>C1COCC1>[CH3:5][C:4]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][N:12]=1)([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 160946965-(Benzyloxy)-2-bromopyridineHCID 178418310HCID 178418310, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 207095055-(Benzyloxy)-2-tert-butylpyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of copper (I) cyanide (18.31 g) in dry THF (400 ml) was added, at −78 C., tertbutylmagnesium chloride (1M in THF, 409 ml). The reaction mixture was stirred at this temperature for 15 min before slowly adding a solution of 2-bromo-5-[(phenylmethyl)oxy]pyridine (13.5 g) in THF. This was stirred for 2 h at −78 C. before warming to 25-30 C. and stirring for a further 20 h. The reaction mixture was poured into water and extracted with ethyl acetate. This was concentrated in vacuo and purified through silica, eluting with 0-2% ethyl acetate in hexane. Appropriate fractions were combined and concentrated in vacuo to yield the title compound, 6.3 g

Workup

  1. stirringThis was stirred for 2 h at −78 C
  2. temperaturebefore warming to 25-30 C
  3. stirringand stirring for a further 20 h
  4. extractionextracted with ethyl acetate
  5. concentrationThis was concentrated in vacuo
  6. custompurified through silica
  7. washeluting with 0-2% ethyl acetate in hexane
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cfc9ccb219cb4008b2f12e8507058a75
Source dataset
uspto-grants-2016_09
Patent number
US09447074B2

Linked notes

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