Sodium hydride → 5-[2-(4-Chloro-phenyl)-thiazol-5-ylmethoxy]-1-methyl-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

HRID 41669Notes

Reaction equation

HRID 41669 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH:13]([OH:15])C)=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:19]1[CH:27]2[CH:22]([C:23]3([CH3:29])[O:28][CH:26]2[CH2:25][CH2:24]3)[C:21](=[O:30])[CH:20]=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([CH2:13][O:15][C:19]3[CH:27]4[CH:22]([C:23]5([CH3:29])[O:28][CH:26]4[CH2:25][CH2:24]5)[C:21](=[O:30])[CH:20]=3)=[CH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 595624751-[2-(4-Chlorophenyl)thiazol-5-yl]ethanolHCID 68568880HCID 68568880, compound

Product 1

HCID 685701795-[2-(4-Chloro-phenyl)-thiazol-5-ylmethoxy]-1-methyl-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-oneYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[2-(4-chloro-phenyl)-thiazol-5-yl]ethanol (264 mg, 1.1 mmol) in tetrahydrofuran (5 ml) is added in one portion the sodium hydride (60% dispersion in mineral oil, 44 mg, 1.1 mmol). The reaction mixture is stirred for five minutes at room temperature and 5-Chloro-1-methyl-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (219 mg, 1.1 mmol) is added in one-portion. The reaction mixture is stirred at room temperature overnight. Silica gel is added to the crude reaction mixture, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give 5-[2-(4-chloro-phenyl)-thiazol-5-ylmethoxy]-1-methyl-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (410 mg).

Workup

  1. stirringThe reaction mixture is stirred at room temperature overnight
  2. additionSilica gel is added to the crude
  3. customreaction mixture
  4. customthe solvent is evaporated under reduced pressure
  5. customthe residue is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-c7dc3997b10d4a78a20b1617ea6715f2
Source dataset
uspto-grants-2013_09
Patent number
US08530667B2

Reaction notes

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