Ethyl 2-phenoxy-5-thiazolecarboxylate → HCID 13106154, compound

HRID 544430Notes

Reaction equation

HRID 544430 reaction equation
[O:1]([C:8]1[S:9][C:10]([C:13](OCC)=[O:14])=[CH:11][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[O:1]([C:8]1[S:9][C:10]([CH2:13][OH:14])=[CH:11][N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 13106142Ethyl 2-phenoxy-5-thiazolecarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 13106154HCID 13106154, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 12 g of the product of Step A in 100 ml of tetrahydrofuran was added dropwise to a mixture of 2.8 g of lithium aluminum hydride in 200 ml of tetrahydrofuran and the mixture was refluxed for 24 hours. Excess hydride was destroyed by addition of ethyl acetate and aqueous 2N hydrochloric acid was added thereto. The mixture was filtered and the aqueous phase was extracted with ether. The combined organic phases were evaporated to dryness to obtain 5.2 g of (2-phenoxy-5-thiazolyl)-methanol.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. customExcess hydride was destroyed by addition of ethyl acetate and aqueous 2N hydrochloric acid
  3. additionwas added
  4. filtrationThe mixture was filtered
  5. extractionthe aqueous phase was extracted with ether
  6. customThe combined organic phases were evaporated to dryness

Sources & evidence

ORD record
ord-0514113b99734879827ca93f68766321
Source dataset
uspto-grants-1984_05
Patent number
US04450169

Reaction notes

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