Lithium Hydroxide → HCID 178521622, compound

HRID 858454Notes

Reaction equation

HRID 858454 reaction equation
C([O:9][C@H:10]1[CH2:13][C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11]1)(=O)C1C=CC=CC=1.[Li+].[OH-]>CO>[C:14]1([C@H:12]2[CH2:11][C@H:10]([OH:9])[CH2:13]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178525789HCID 178525789, compound

Product 1

HCID 178521622HCID 178521622, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of trans-3-phenylcyclobutyl benzoate (step 1, 6.5 g, 26.0 mmol) in methanol (100 mL) was added 4N aqueous LiOH (20 mL, 80 mmol) and the resulting mixture was stirred at room temperature for 10 min. The mixture was concentrated. The residue was dissolved in water (100 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with brine (100 mL), dried (Na2SO4), and concentrated. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (5:1) to afford 3.65 g (93%) of the title compound as a colorless oil: 1H-NMR (CDCl3) δ 7.34–7.16 (5H, m), 4.60–4.51 (1H, m), 3.69–3.59 (1H, m), 2.55–2.37 (4H, m).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionThe residue was dissolved in water (100 mL)
  3. extractionextracted with ethyl acetate (100 mL)
  4. washThe organic layer was washed with brine (100 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-16b6d9542fe643008206f1eb7ae0889c
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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