Hydrochloric Acid → HCID 59562431, compound

HRID 1849961Notes

Reaction equation

HRID 1849961 reaction equation
[H-].[Na+].[Br:3][C:4]1[S:5][C:6]([CH2:9][OH:10])=[CH:7][N:8]=1.Cl[C:12]1[C:17]([CH3:19])([CH3:18])[C:16](=[O:20])[C:15]([CH3:22])([CH3:21])[C:14](=[O:23])[CH:13]=1.Cl>O1CCCC1.O>[Br:3][C:4]1[S:5][C:6]([CH2:9][O:10][C:12]2[C:17]([CH3:18])([CH3:19])[C:16](=[O:20])[C:15]([CH3:22])([CH3:21])[C:14](=[O:23])[CH:13]=2)=[CH:7][N:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 7213124(2-Bromo-1,3-thiazol-5-yl)methanolHCID 67524164HCID 67524164, compound

Product 1

HCID 59562431HCID 59562431, compoundYield 53.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of sodium hydride, 60% dispersion in mineral oil solution (1.6 g, 40 mmol) in tetrahydrofuran (50 ml) is added a solution of (2-bromothiazol-5-yl)methanol (6.75 g, 35 mmol) in tetrahydrofuran (50 ml) at 0° C. A solution of 5-chloro-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione (7.0 g, 35 mmol) in tetrahydrofuran (50 ml) is then added and the reaction mixture is heated to reflux for 18 hours. The reaction mixture is poured into water, acidified to pH4 with dilute aqueous hydrochloric acid and extracted with ethyl acetate (4×50 ml). The combined organic layers are dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated to a brown oil. The crude product is purified by flash chromatography on silica gel to give 5-(2-bromothiazol-5-ylmethoxy)-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione (6.75 g).

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux for 18 hours
  3. extractionextracted with ethyl acetate (4×50 ml)
  4. dry with materialThe combined organic layers are dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate is evaporated to a brown oil
  7. customThe crude product is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-96183d183dfa4208b9d1024a73a60375
Source dataset
uspto-grants-2015_02
Patent number
US08956999B2

Reaction notes

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