Ethyl Acetate → HCID 59296194, compound

HRID 2233553Notes

Reaction equation

HRID 2233553 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][C:12]1[N:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([F:29])([F:28])([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[S:15][C:16]=1[CH3:17])C.C(OCC)(=O)C.[NH4+].[Cl-]>O1CCCC1>[CH3:17][C:16]1[S:15][C:14]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([F:29])([F:27])([F:25])([F:26])[F:28])=[CH:20][CH:19]=2)=[N:13][C:12]=1[CH2:11][CH2:10][OH:9]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 59296133HCID 59296133, compound

Product 1

HCID 59296194HCID 59296194, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

458 mg Lithium aluminium hydride were suspended in 100 ml dry tetrahydrofuran and cooled in an ice bath. To this ice cooled suspension were added 4.5 g [5-Methyl-2-(4-pentafluorosulfanyl-phenyl)-thiazol-4-yl]-acetic acid ethyl ester, dissolved in 50 ml tetrahydrofuran. The reaction mixture was stirred for one hour. Then 300 ml ethyl acetate and 20 ml saturated NH4Cl solution were added. The organic layer was separated. The aqueous phase was extracted three times with portions of 50 ml ethyl acetate. The combined organic layers were dried over MgSO4 and the solvent was removed in vacuo. The residue was purified by flash chromatography with the eluent n-heptane:ethyl acetate=2:1 to provide 1.44 g 2-[5-methyl-2-(4-pentafluorosulfanyl-phenyl)-thiazol-4-yl]-ethanol as an oil which solidified upon standing.

Workup

  1. temperaturecooled in an ice bath
  2. customThe organic layer was separated
  3. extractionThe aqueous phase was extracted three times with portions of 50 ml ethyl acetate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by flash chromatography with the eluent n-heptane

Sources & evidence

ORD record
ord-2571f702e2df4449a084a47ed373b2a3
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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