Lithium hydroxide, monohydrate → HCID 10273808, compound

HRID 394928Notes

Reaction equation

HRID 394928 reaction equation
[CH3:1][C:2]1([CH3:32])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C@@H:14]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:15][O:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2.O.[OH-].[Li+]>C1COCC1.O.CCOCC>[CH3:1][C:2]1([CH3:32])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C@@H:14]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:15][O:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=3)[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69683369HCID 69683369, compound

Product 1

HCID 10273808HCID 10273808, compoundYield 82.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The ester (1 g), dissolved in 20 ml THF/5 ml H2O/5 ml methanol, was treated with 380 mg of lithium hydroxide hydrate. The mixture was stirred at room temperature 4 hours. The mixture was diluted with 50 ml water and acidified to pH 2 with 1N hydrochloric. The resulting suspension was taken in 100 ml ether and the phases were separated. The aqueous phase was extracted with three portions of 50 ml ether. The combined extracts were dried over MgSO4. The solvent was removed in vacuo and the crude product was purified recrystalization from acetonitrile/water, yielding 796 mg of product as shining platelets. M.p. 74-76° C., [α]D=−22.2 (c=0.500, in CHCl3).

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with three portions of 50 ml ether
  3. dry with materialThe combined extracts were dried over MgSO4
  4. customThe solvent was removed in vacuo
  5. customthe crude product was purified
  6. customrecrystalization from acetonitrile/water

Sources & evidence

ORD record
ord-e4ae2b9b0f904544a26b6bcb64bec9d1
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

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