Lithium hydroxide, monohydrate → HCID 22736530, compound

HRID 51066Notes

Reaction equation

HRID 51066 reaction equation
[CH3:1][CH:2]([CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1([C:12]([O:14]C)=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8]1.O.[OH-].[Li+]>C1COCC1.O.Cl>[CH3:1][CH:2]([CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1([C:12]([OH:14])=[O:13])[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22736519Methyl 1-(5-methylhexyl)cyclopentanecarboxylate

Product 1

HCID 22736530HCID 22736530, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-(5-methyl-hexyl)cyclopentanecarboxylate (110 mg, 0.4 mmol) in 21 mL of THF cooled to 0° C. was added dropwise a solution of lithium hydroxide monohydrate (26 mg, 0.6 mmol) in 5.0 mL of water. The reaction mixture was stirred at rt for 16 h. THF was removed under reduced pressure to give a yellow oil which was diluted with 10 mL of 1 N HCl. The aqueous phase was extracted with CH2Cl2 (8×15 mL), and the extracts were combined, dried over Na2SO4, and concentrated to afford 60 mg (71%) of the desired product. MS [M+H]+213.

Workup

  1. customTHF was removed under reduced pressure
  2. customto give a yellow oil which
  3. extractionThe aqueous phase was extracted with CH2Cl2 (8×15 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-313b254006824e0cb790e676c1c61071
Source dataset
uspto-grants-2004_03
Patent number
US06713476B2

Reaction notes

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