Water → 4-(4-Fluorophenyl)-2-methyl-5-thiazolemethanol

HRID 1181321Notes

Reaction equation

HRID 1181321 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH3:18])[S:11][C:12]=2[C:13](OCC)=[O:14])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH3:18])[S:11][C:12]=2[CH2:13][OH:14])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21943122HCID 21943122, compound

Product 1

HCID 99209004-(4-Fluorophenyl)-2-methyl-5-thiazolemethanolYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-(4-fluorophenyl)-2-methyl-5-thiazolecarboxylate (59 g) prepared by a known method (Chem. Pharm. Bull., 43(6), 947, 1995) was dissolved in tetrahydrofuran (700 ml). Lithium aluminum hydride (13 g) was added under ice-cooling and the mixture was stirred for 30 min. Water (13 ml), 15% sodium hydroxide (13 ml) and water (39 ml) were added successively to the reaction mixture, and the precipitated insoluble materials were filtered off. The filtrate was concentrated under reduced pressure to give the title compound (37 g, yield 71%).

Workup

  1. temperaturecooling
  2. filtrationthe precipitated insoluble materials were filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ce9b3cdc31e241d1adc5d958971075da
Source dataset
uspto-grants-2007_10
Patent number
US07285551B2

Reaction notes

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