Pyridine → Carbonic acid 3-(3-cyano-phenoxy)-4-methoxy-benzyl ester methyl ester

HRID 332580Notes

Reaction equation

HRID 332580 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:18][CH3:19])=[C:7]([CH:17]=1)[O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13].N1C=CC=CC=1.Cl[C:27]([O:29][CH3:30])=[O:28]>O1CCCC1>[CH3:30][O:29][C:27](=[O:28])[O:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:18][CH3:19])=[C:7]([O:8][C:9]2[CH:16]=[CH:15][CH:14]=[C:11]([C:12]#[N:13])[CH:10]=2)[CH:17]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 577011193-(5-Hydroxymethyl-2-methoxy-phenoxy)-benzonitrile

Product 1

HCID 57701117Carbonic acid 3-(3-cyano-phenoxy)-4-methoxy-benzyl ester methyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an 40 mL vial equipped with a stir bar was placed (17) (940 mg, 3.68 mmol), anhydrous tetrahydrofuran (18 mL) and pyridine (774 μL, 9.57 mmol). The resulting clear solution was cooled in an ice water bath for 10 minutes and then methyl chloroformate (626 μL, 8.10 mmol) was added and reaction mixture was slowly warmed to room temperature and reacted for 16 hours. The reaction was concentrated by a stream of nitrogen followed by treatment with water (50 mL) and 1M HCl (40 mL). The aqueous portion was extracted with dichloromethane (3×50 mL). The organic portions were combined, washed with brine (50 mL), dried (MgSO4) and concentrated to produce 1.09 g (95% yield) of (18) as a colorless, viscous oil.

Workup

  1. customIn an 40 mL vial equipped with a stir bar
  2. temperatureThe resulting clear solution was cooled in an ice water bath for 10 minutes
  3. customreaction mixture
  4. customreacted for 16 hours
  5. concentrationThe reaction was concentrated by a stream of nitrogen
  6. extractionThe aqueous portion was extracted with dichloromethane (3×50 mL)
  7. washwashed with brine (50 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-00af26ff232e4e4b8d8c5f40afbaca1b
Source dataset
uspto-grants-2014_11
Patent number
US08877816B2

Reaction notes

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