Bicarbonate Ion → methyl 5-((4-fluorophenyl) (hydroxy)methyl)-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylate

HRID 2061553Notes

Reaction equation

HRID 2061553 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[CH:10]([C:12]1[CH:17]=[N:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[C:14]2[O:22][C:23]([CH3:27])([CH3:26])[O:24][CH2:25][C:13]=12)=[O:11].C(=O)(O)[O-]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:10]([OH:11])[C:12]2[CH:17]=[N:16][C:15]([C:18]([O:20][CH3:21])=[O:19])=[C:14]3[O:22][C:23]([CH3:26])([CH3:27])[O:24][CH2:25][C:13]=23)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 769Bicarbonate IonHCID 58360280methyl 5-formyl-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylateHCID 178418676HCID 178418676, compound

Product 1

HCID 67294267methyl 5-((4-fluorophenyl) (hydroxy)methyl)-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylateYield 47%

Conditions

Temperature
-78 °C

Procedure

A 4-fluorophenyl magnesium bromide solution (0.438 mL of 1M in tetrahydrofuran, 30.0 mmol, 1.1 eq) at −78° C. was added to a methyl 5-formyl-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylate solution (0.100 g, 0.398 mmol, 1 eq. in 5.0 mL of tetrahydrofurane). The reaction mixture was stirred for 20 min. at −78° C. A saturated bicarbonate solution was added and reaction mixture was extracted with ethyl acetate. The organic phases were combined, dried over magnesium sulphate and concentrated under reduced pressure yielding 0.065 g of crude product methyl 5-((4-fluorophenyl)(hydroxy)methyl)-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylate 2a (47% yield) as a white solid.

Workup

  1. customreaction mixture
  2. extractionwas extracted with ethyl acetate
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-adc8209ecf7c4fd89d5f67562a9a5d26
Source dataset
uspto-grants-2012_10
Patent number
US08283366B2

Reaction notes

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