Carbon Dioxide → HCID 86731410, compound

HRID 2277322Notes

Reaction equation

HRID 2277322 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][O:17][CH3:18])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19](=[O:21])=[O:20].Cl>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:12]([O:15][CH2:16][O:17][CH3:18])=[CH:11][N:10]=1)[C:19]([OH:21])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 672176842-(Benzyloxy)-5-(methoxymethoxy)pyridine

Product 1

HCID 86731410HCID 86731410, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(benzyloxy)-5-(methoxymethoxy)pyridine (8.00 g) in THF (50 mL) was added 1.6 M n-butyllithium-hexane solution (30.6 mL) at −78° C., and the mixture was stirred at the same temperature for 1 hr. To the reaction mixture was added an excess amount of dry ice, and the mixture was allowed to warm to room temperature. 1 M Hydrochloric acid was added thereto, and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (9.30 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layer were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-94d627c5f6ac4025bcbbea1c2072efd0
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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