Lithium hydroxide, monohydrate → HCID 67168907, compound

HRID 872923Notes

Reaction equation

HRID 872923 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([C:15]([O:17]CC)=[O:16])[CH:11]=1.O.[OH-].[Li+]>C1COCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([C:15]([OH:17])=[O:16])[CH:11]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrate2×HCID 67169035HCID 67169035, compound

Product 1

HCID 67168907HCID 67168907, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)isoxazole-3-carboxylate (1.77 g, 6.57 mmol) was dissolved in THF (20 ml). 1M lithium hydroxide monohydrate (6.57 ml) was added and the resulting mixture stirred at RT for 2 h. During the same day more of 1M lithium hydroxide monohydrate (19.71 ml in total) was added and the reaction mixture was stirred overnight. THF was evaporated, water was added and the pH was adjusted to 4 with citric acid solution. The mixture was extracted four times with ethyl acetate. The combined organic layers were dried and evaporated. LC-MS: [M+1]=242.24.

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customTHF was evaporated
  3. additionwater was added
  4. extractionThe mixture was extracted four times with ethyl acetate
  5. customThe combined organic layers were dried
  6. customevaporated

Sources & evidence

ORD record
ord-8137e377dccd428594dee0a8895aa5bf
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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