Sodium hydride → HCID 59562463, compound

HRID 1849965Notes

Reaction equation

HRID 1849965 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH:13]([OH:15])[CH3:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:19]1[C:24]([CH3:26])([CH3:25])[O:23][C:22]([CH3:28])([CH3:27])[C:21](=[O:29])[CH:20]=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([CH:13]([O:15][C:19]3[C:24]([CH3:25])([CH3:26])[O:23][C:22]([CH3:28])([CH3:27])[C:21](=[O:29])[CH:20]=3)[CH3:14])=[CH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 59562418HCID 59562418, compoundHCID 595624751-[2-(4-Chlorophenyl)thiazol-5-yl]ethanol

Product 1

HCID 59562463HCID 59562463, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-[2-(4-chlorophenyl)thiazol-5-yl]ethanol (335 mg, 1.4 mmol) in anhydrous tetrahydrofuran (5 ml) under nitrogen is added sodium hydride, 60% dispersion in mineral oil, (48 mg, 1.2 mmol) and the resulting yellow suspension is allowed to stir at room temperature for 1 hour. A solution of 5-chloro-2,2,6,6-tetramethyl-6H-pyran-3-one (189 mg, 1 mmol) in anhydrous tetrahydrofuran (2 ml) is then added and reaction is allowed to stir at room temperature for 17 hours. The crude reaction mixture is purified by flash chromatography on silica gel to give 5-{1-[2-(4-chlorophenyl)thiazol-5-yl]ethoxy}-2,2,6,6-tetramethyl-6H-pyran-3-one (288 mg).

Workup

  1. customreaction
  2. stirringto stir at room temperature for 17 hours
  3. customThe crude reaction mixture
  4. customis purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-577d5312384042059e5c0c557905678f
Source dataset
uspto-grants-2015_02
Patent number
US08956999B2

Reaction notes

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