Water → HCID 10909824, compound

HRID 577093Notes

Reaction equation

HRID 577093 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][CH:8]([C:10]1[N:11]=[CH:12][S:13][C:14]=1[C:15](OCC)=[O:16])[CH3:9].O.CCOC(C)=O>C1COCC1>[CH3:7][CH:8]([C:10]1[N:11]=[CH:12][S:13][C:14]=1[CH2:15][OH:16])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 13015600Ethyl 4-isopropylthiazole-5-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10909824HCID 10909824, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. mixture of lithium aluminum hydride (300 mg, 7.9 mmol) in anhydrous THF (10 mL) was slowly added a solution of ethyl 4-(propan-2-yl)-1,3-thiazole-5-carboxylate (1.06 g, 6.1 mmol) in anhydrous THF (10 mL). The reaction mixture was stirred at room temperature for 1.5 hours. After cooling to 0° C., water (20 mL) and EtOAc (40 mL) were added. The mixture was stirred for 30 minutes. The solid material was removed by filtration. The organic layer was recovered. The aqueous layer was extracted with EtOAc (2×20 mL). The combined organic extracts were dried over MgSO4, filtered, evaporated, and dried in vacuo, affording [4-(propan-2-yl)-1,3-thiazol-5-yl]methanol (802 mg, 96% yield). The product was used without further purification.

Workup

  1. temperatureAfter cooling to 0° C.
  2. stirringThe mixture was stirred for 30 minutes
  3. customThe solid material was removed by filtration
  4. customThe organic layer was recovered
  5. extractionThe aqueous layer was extracted with EtOAc (2×20 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customdried in vacuo

Sources & evidence

ORD record
ord-07a8219d215d466abe9eb8cf1d1b797b
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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