Hydrochloric Acid → HCID 58934102, compound

HRID 2103430Notes

Reaction equation

HRID 2103430 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 94.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminium hydride (1.2 g) in dry tetrahydrofuran (100 mL) add 4-butyl-2-(4-trifluormethyl-phenyl)-thiazol-5-carboxylic acid methyl ester (5.3 g, 15.4 mmol) dissolved in tetrahydrofuran (100 mL). Stir the reaction mixture at room temperature over a period of one hour. Add a saturated aqueous solution of ammonium chloride (50 mL) and then a 1 molar aqueous solution of hydrochloric acid (50 mL). Extract the reaction mixture five times with portions of 60 ml of ethyl acetate. Dry the combined extracts with MgSO4 and remove the solvent under reduced pressure to provide [4-butyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-yl]-methanol (4.6 g) as a yellow oil, which solidified upon standing at room temperature.

Workup

  1. extractionExtract the reaction mixture five times with portions of 60 ml of ethyl acetate
  2. dry with materialDry the combined extracts with MgSO4
  3. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-d557d81872a1403986538d30a3b9cf98
Source dataset
uspto-grants-2009_08
Patent number
US07576109B2

Reaction notes

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