Lithium hydroxide, monohydrate → HCID 22731980, compound

HRID 2083905Notes

Reaction equation

HRID 2083905 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH3:13])[CH:11]=1)[S:8][CH2:7][CH2:6][C:5]2([C:15]([O:17]CC)=[O:16])[OH:14].O.[OH-].[Li+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH3:13])[CH:11]=1)[S:8][CH2:7][CH2:6][C:5]2([C:15]([OH:17])=[O:16])[OH:14]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 11301123HCID 11301123, compound

Product 1

HCID 22731980HCID 22731980, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice/water-cooled solution of 6-chloro-4-hydroxy-8-methoxythiochromane-4-yl-carboxylic acid, ethyl ester (2.26 g, 7.46 mmol; see step (iv) above) in THF (20 mL) was added a solution of lithium hydroxide monohydrate (0.68 g, 16 mmol) in water (10 mL). The temperature was allowed to slowly rise to ambient overnight. THF was removed in vacuo, the residue was washed with diethyl ether, acidified with 2 M aq. HCl and then extracted with ethyl acetate. Drying (MgSO4) and removal of the solvent in vacuo afforded the sub-title compound.

Workup

  1. customTHF was removed in vacuo
  2. washthe residue was washed with diethyl ether
  3. extractionextracted with ethyl acetate
  4. customDrying
  5. custom(MgSO4) and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-f593f93b05714c3a882bfdc630062029
Source dataset
uspto-grants-2004_04
Patent number
US06716834B2

Reaction notes

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