Hydrochloric Acid → HCID 58934102, compound

HRID 2233546Notes

Reaction equation

HRID 2233546 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[S:15][C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[N:13][C:12]=1[CH2:26][CH2:27][CH2:28][CH3:29])=O.[Cl-].[NH4+].Cl>O1CCCC1>[CH2:26]([C:12]1[N:13]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:18][CH:17]=2)[S:15][C:11]=1[CH2:9][OH:8])[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 57713028HCID 57713028, compound

Product 1

HCID 58934102HCID 58934102, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.2 g lithium aluminium hydride was dissolved in 100 ml dry tetrahydrofuran. 5.3 g 4-Butyl-2-(4-trifluormethyl-phenyl)-thiazol-5-carboxylic acid methyl ester, dissolved in 100 ml tetrahydrofuran, were added. The reaction mixture was stirred at room temperature over a period of one hour, then 50 ml saturated ammonium chloride solution and 50 ml of a 1 molar hydrochloric acid solution were added. The reaction mixture was extracted five times with portions of 60 ml of ethyl acetate. The combined organic layers were dried over MgSO4 and the solvent removed under reduced pressure to provide 4.6 g [4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-yl]-methanol as a yellow oil, which solidified upon standing at room temperature.

Workup

  1. additionwere added
  2. extractionThe reaction mixture was extracted five times with portions of 60 ml of ethyl acetate
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-0b8f3886c8684a54adab89f99e4ca682
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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