Sodium hydride → 5-(5-Bromothiophen-2-ylmethoxy)-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione

HRID 1849960Notes

Reaction equation

HRID 1849960 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH2:7][OH:8])=[CH:4][CH:3]=1.[H-].[Na+].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>O1CCCC1>[Br:1][C:2]1[S:6][C:5]([CH2:7][O:8][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:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11435467(5-bromothien-2-yl)methanolHCID 67524164HCID 67524164, compound

Product 1

HCID 595624695-(5-Bromothiophen-2-ylmethoxy)-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dioneYield 49.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromothiophen-2-ylmethanol (6.76 g, 35 mmol) in tetrahydrofuran (100 ml) at 0° C. is added, carefully, sodium hydride, 60% dispersion in mineral oil, (1.2 g, 30 mmol over a period of 10 minutes. The reaction is allowed to warm to room temperature and stirred for a further hour. 5-Chloro-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione (5.02 mg, 25 mmol) is then added in one portion and the reaction mixture is allowed to stir at room temperature for 17 hours. The reaction is concentrated in vacuo and purified by flash chromatography on silica gel to give the desired compound as a white solid (4.45 g)

Workup

  1. stirringto stir at room temperature for 17 hours
  2. concentrationThe reaction is concentrated in vacuo
  3. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-082120e6f85d4bdda2bc1748af0bdc62
Source dataset
uspto-grants-2015_02
Patent number
US08956999B2

Reaction notes

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