Bicarbonate Ion → HCID 67294286, compound

HRID 1183111Notes

Reaction equation

HRID 1183111 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:18]([O:20][CH3:21])=[O:19])=[N:11][CH:12]=[C:13]([CH:16]=[O:17])[C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([Mg]Br)=[CH:25][CH:24]=1.C(=O)(O)[O-]>O1CCCC1>[CH2:1]([O:8][C:9]1[C:10]([C:18]([O:20][CH3:21])=[O:19])=[N:11][CH:12]=[C:13]([CH:16]([C:26]2[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=2)[OH:17])[C:14]=1[CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 769Bicarbonate IonHCID 86656080HCID 86656080, compoundHCID 178418676HCID 178418676, compound

Product 1

HCID 67294286HCID 67294286, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.0 g of methyl 3-(benzyloxy)-5-formyl-4-methylpicolinate (3.50 mmol, 1 eq) was dissolved in 20.0 mL of tetrahydrofuran and 4.2 mL of a 4-fluorophenyl magnesium bromide solution (1M in tetrahydrofuran, 4.20 mmol, 1.2 eq) was added at −78° C. over a period of 1 hr. The reaction mixture was then stirred for 20 min. −78° C. A saturated bicarbonate solution was added and reaction mixture was extracted with ethyl acetate.

Workup

  1. customreaction mixture
  2. extractionwas extracted with ethyl acetate

Sources & evidence

ORD record
ord-6f64018ce38c425baaf4e05d27895f20
Source dataset
uspto-grants-2014_03
Patent number
US08664248B2

Reaction notes

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