Lithium hydroxide, monohydrate → HCID 60004015, compound

HRID 133012Notes

Reaction equation

HRID 133012 reaction equation
[CH3:1][CH:2]([CH3:19])[CH2:3][C@H:4]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:5]([O:7]CCCCC)=[O:6].O.[OH-].[Li+]>C1COCC1.O.Cl>[CH3:1][CH:2]([CH3:19])[CH2:3][C@H:4]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 60004009HCID 60004009, compound

Product 1

HCID 60004015HCID 60004015, compoundYield 74.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S)-pentyl 4-methyl-2-pentyloxypentanoate 2 (80 mg, 0.3 mmol) in 20 mL of THF cooled to 0° C. was added dropwise a solution of lithium hydroxide monohydrate (25 mg, 0.6 mmol) in 5 mL of water. The reaction mixture was stirred at rt for 16 h. THF was removed under reduced pressure to give an 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 compound 10 (45 mg, 74%). MS [M+H]+ 203.

Workup

  1. customTHF was removed under reduced pressure
  2. customto give an 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-13c3237310294c01b6643abbe73ef8ec
Source dataset
uspto-grants-2008_06
Patent number
US07390802B2

Reaction notes

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