Bicarbonate Ion → HCID 67294286, compound

HRID 2061555Notes

Reaction equation

HRID 2061555 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, compoundYield 52.4%

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. The resulting organic phases were combined, dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by silica gel (50% ethyl acetate/hexane) yielding 0.70 g of colourless oil containing the desired product 7a (53% yield).

Workup

  1. customreaction mixture
  2. extractionwas extracted with ethyl acetate
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by silica gel (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0942bb75105c40cd9a511a911f1c6b69
Source dataset
uspto-grants-2012_10
Patent number
US08283366B2

Reaction notes

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