Aluminium lithium hydride → 2-Phenyl-1,3-thiazole-4-carbaldehyde

HRID 70030Notes

Reaction equation

HRID 70030 reaction equation
COCN[C:5]([C:7]1[N:8]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:10][CH:11]=1)=[O:6].[H-].[H-].[H-].[H-].[Li+].[Al+3].C1(C2SC=C(C(C3C=C(OC)C(OC)=C(OC)C=3)=O)N=2)C=CC=CC=1>C1COCC1>[C:12]1([C:9]2[S:10][CH:11]=[C:7]([CH:5]=[O:6])[N:8]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 252274304-(3,4,5-Trimethoxybenzoyl)-2-phenylthiazoleHCID 575168322-Phenyl-thiazole-4-carboxylic acid methoxymethylamide

Product 1

HCID 7365242-Phenyl-1,3-thiazole-4-carbaldehydeYield 45.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At −78° C., to a solution of 2-phenyl-thiazole-4-carboxylic acid methoxymethylamide (1 equiv) in THF was added LiAlH4 (1 equiv, 1 N in THF) and stirring for 1h at −20° C. The reaction mixture was placed on an ice bath and quenched by 20% H2SO4 solution, extracted with ethyl acetate and dried over MgSO4. The solvent was removed under reduced pressure and purified by column chromatography to yield 42b (45.8%). NMR (300 MHz, CDCl3) δ 10.1 (s, 1H), 8.17 (s, 1H), 8.02-8.00 (m, 2H), 7.50-7.48 (m, 3H). MS (ESI) m/z 244.1 (M+Na+MeOH)+.

Workup

  1. customThe reaction mixture was placed on an ice bath
  2. customquenched by 20% H2SO4 solution
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-939bd99b57fd4548a5d383af6aae6d28
Source dataset
uspto-grants-2014_09
Patent number
US08822513B2

Reaction notes

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