Hydrochloric Acid → HCID 58934102, compound

HRID 1983552Notes

Reaction equation

HRID 1983552 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 aluminum hydride were dissolved in 100 ml dry tetrahydro-furan. 5.3 g 4-Butyl-2-(4-trifluormethyl-phenyl)-thiazol-5- carboxylic acid methyl ester, dissolved in 100 ml tetrahydro-furan, 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 was 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-cab93090d6b541f8abad2703e3ca2e05
Source dataset
uspto-grants-2009_06
Patent number
US07541464B2

Reaction notes

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