Lithium Hydroxide → HCID 57448174, compound

HRID 1667583Notes

Reaction equation

HRID 1667583 reaction equation
[CH:1]1([S:5][C:6]2[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=2[C:8]([O:10]C)=[O:9])[CH2:4][CH2:3][CH2:2]1.[Li+].[OH-]>C1COCC1>[CH:1]1([S:5][C:6]2[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=2[C:8]([OH:10])=[O:9])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57448173Methyl 2-(cyclobutylsulfanyl)benzoate

Product 1

HCID 57448174HCID 57448174, compoundYield 106.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2A (7.20 g, 28.3 mmol) in THF (190 mL) was added 1 N LiOH (94 mL). The reaction was stirred for 1 h at rt, then was heated gradually to 65° C. After cooling to rt, the THF was removed under reduced pressure. The remaining solution was cooled to 0° C. and acidified to pH 1 with 1N HCl. The product was extracted with CH2Cl2, and the organic layer was washed with brine, dried (MgSO4), filtered and concentrated to provide 2B as a clear oil (6.30 g). LC-MS: 241.08 (M+H)+.

Workup

  1. temperaturewas heated gradually to 65° C
  2. temperatureAfter cooling to rt
  3. customthe THF was removed under reduced pressure
  4. temperatureThe remaining solution was cooled to 0° C.
  5. extractionThe product was extracted with CH2Cl2
  6. washthe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f8a1336871e84211aae0d1f172d70e13
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

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