Lithium Hydroxide → HCID 90003241, compound

HRID 587865Notes

Reaction equation

HRID 587865 reaction equation
[C:1]12(OCC[O:18]1)[C:10]1[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:4][C@@H:3]([CH2:11][CH2:12][C:13]([O:15]CC)=[O:14])[CH2:2]2.[Li+].[OH-]>C1COCC1.O>[O:18]=[C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:2]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 131734417HCID 131734417, compound

Product 1

HCID 90003241HCID 90003241, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of (R)-ethyl 3-(3′,4′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-naphthalen]-3′-yl)propanoate (2.3 g, 7.92 mmol) in THF (10 mL) and water (1 mL) in round bottom flask. LiOH (1.328 g, 55.4 mmol) was added and reaction mixture was stirred at 25° C. for 2 h. Reaction mixture was concentrated and acidified with dilute HCl, stirred for 1 h at RT. Extracted with ethyl acetate (2×30 mL), dried over sodium sulphate, concentrated to get crude title compound (1.6 g, 93%); m/z 262.7

Workup

  1. customreaction mixture
  2. customReaction mixture
  3. concentrationwas concentrated
  4. stirringstirred for 1 h at RT
  5. extractionExtracted with ethyl acetate (2×30 mL)
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7e8a89922246439490adf4a2db38c7c9
Source dataset
uspto-grants-2016_01
Patent number
US09227919B2

Reaction notes

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