Water → Methyl 3-benzyloxy-6-phenylpicolinate

HRID 274882Notes

Reaction equation

HRID 274882 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:16]([O:18][CH3:19])=[O:17])=[N:11][C:12](Cl)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1(OB(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH2:1]([O:8][C:9]1[C:10]([C:16]([O:18][CH3:19])=[O:17])=[N:11][C:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 20088900Methyl 3-benzyloxy-6-chloropicolinate

Product 1

HCID 20088897Methyl 3-benzyloxy-6-phenylpicolinate

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent3×

Procedure

0.6 g (0.5 mmol) of tetrakis(triphenylphosphine)palladium(O) and 5 ml of 1,2-dimethoxyethane were charged in a 100 ml three-forked flask equipped with a thermometer, a cooling tube and a nitrogen-introducing tube. Thereafter, 2.7 g (10.0 mmol) of methyl 3-benzyloxy-6-chloropicolinate was dissolved in 1,2-dimethoxyethane (20 ml) under nitrogen stream, and was added to the flask at one time. After stirring the resultant mixture at room temperature for 3 hours, 1.8 g (15.0 mmol) of phenylboric acid was dissolved in 1,2-dimethoxyethane (15 ml) and was added to the reaction mixture, which was further stirred for 1 hour. Thereafter, 2M-sodium carbonate aqueous solution (40 ml) was added to the reaction mixture, and the resultant mixture was heat-refluxed for 50 minutes. After cooling, an appropriate amount of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer thus obtained was washed with water and saturated salt water, dried and concentrated, and the residue thus obtained was purified by column chromatography to obtain an aimed compound.

Workup

  1. customequipped with a thermometer, a cooling tube
  2. additiona nitrogen-introducing tube
  3. additionwas added to the flask at one time
  4. additionwas added to the reaction mixture, which
  5. temperatureAfter cooling
  6. extractionthe mixture was extracted with ethyl acetate
  7. customThe organic layer thus obtained
  8. washwas washed with water and saturated salt water
  9. customdried
  10. concentrationconcentrated
  11. customthe residue thus obtained
  12. customwas purified by column chromatography

Sources & evidence

ORD record
ord-e51aa7d296c44efba19a847fe3cdf71a
Source dataset
uspto-grants-1995_02
Patent number
US05391537

Reaction notes

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