Diethyl Ether → HCID 15190126, compound

HRID 1033735Notes

Reaction equation

HRID 1033735 reaction equation
C1([C@H](C)C([O:10][CH2:11][C:12]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=2[F:34])([OH:26])[C:13]([S:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)([CH3:15])[CH3:14])=O)C=CC=CC=1.O.[OH-].[Li+].C(OCC)C>C1COCC1.O>[F:34][C:28]1[CH:29]=[C:30]([F:33])[CH:31]=[CH:32][C:27]=1[C:12]([OH:26])([C:13]([S:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)([CH3:15])[CH3:14])[CH2:11][OH:10]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 168937Lithium hydroxide, monohydrateHCID 53764990HCID 53764990, compound

Product 1

HCID 15190126HCID 15190126, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixed solvent of 100 ml of THF and 30 ml of water was dissolved 10.0 g (20.0 mmol) of 2-(2,4-difluorophenyl)-2-hydroxy-3-((4-methoxyphenyl)methylthio)-3-methylbutyl (S)-(+)-2-phenylpropionate ([α]25 +15.9° (c=1.09, MeOH)), and 1.68 g (40.0 mmol) of lithium hydroxide monohydrate was added thereto in divided portions with stirring under ice-cooling. The mixture was warmed to room temperature and stirred for 30 hours. To the reaction mixture was added diethyl ether, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with a saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution and dried. The solvent was removed by distillation under reduced pressure, and the residue was subjected to column chromatography using a mixed solvent of hexane and ethyl acetate (5:1) as an eluent. The solvent was removed by distillation under reduced pressure to obtain 7.3 g (99%) of (+)-2-(2,4-difluorophenyl)-3-((4-methoxyphenyl)methylthio)-3-methylbutane-1,2 -diol as a colorless oily substance.

Workup

  1. additionwas added
  2. temperaturecooling
  3. stirringstirred for 30 hours
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed successively with a saturated sodium hydrogencarbonate aqueous solution
  6. dry with materiala saturated sodium chloride aqueous solution and dried
  7. customThe solvent was removed by distillation under reduced pressure
  8. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-f9f2304572ef43ac9df90e893b73af74
Source dataset
uspto-grants-1994_05
Patent number
US05312815

Reaction notes

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