Hydrochloric Acid → 40500-07-0

HRID 397726Notes

Reaction equation

HRID 397726 reaction equation
[OH-].[Li+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[CH2:9][CH2:10][C:11]([O:13]C)=[O:12].Cl>O1CCCC1>[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[CH2:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 11095085HCID 11095085, compound

Product 1

HCID 2223651840500-07-0Yield 108.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 2M aqueous solution of lithium hydroxide (4 ml) was added to a solution of methyl 3-(tetrahydropyran-2-yl)propanoate (Preparation 25, 460 mg, 2.67 mmol) in tetrahydrofuran (16 ml) and the reaction mixture was heated under reflux for 10 h. The cooled reaction mixture was acidified with 2N aqueous hydrochloric acid to pH 1 and extracted with ethyl acetate (3×50 ml). The combined extracts were washed with brine (30 ml), dried (MgSO4), filtered and concentrated in vacuo to give the title compound as a colourless oil (460 mg, 67%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 10 h
  3. customThe cooled reaction mixture
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. washThe combined extracts were washed with brine (30 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3769e7c605bd41f9975ef254e9452731
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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