Lithium hydroxide, monohydrate → HCID 89704746, compound

HRID 1481320Notes

Reaction equation

HRID 1481320 reaction equation
C[O:2][C:3]([CH:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[O:7][CH2:6]1)=[O:4].O[Li].O>CCO.CO.O.CCOC(C)=O>[O:7]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:13]2[CH:5]([C:3]([OH:4])=[O:2])[CH2:6]1

Participants

7

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 117819008HCID 117819008, compound

Product 1

HCID 89704746HCID 89704746, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,3-dihydrofuro[2,3-b]pyridine-3-carboxylic acid methyl ester (21.2 mmol) in 20 mL EtOH and 15 mL MeOH was added a solution of LiOH.H2O (23.3 mmol) in 6 mL H2O. After stirring at RT for 1 h, the reaction mixture was diluted with 20 mL EtOAc and extracted twice with water. The water phase was acidified to pH 3 and extracted 5 times with EtOAc and 3 times with DCM. The combined organic layers were dried over MgSO4 and concentrated in vacuo to obtain the desired product as beige solid.

Workup

  1. extractionextracted twice with water
  2. extractionextracted 5 times with EtOAc and 3 times with DCM
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6875228555574808ae1665280fc86c05
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

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