tert-Butanol → HCID 90281979, compound

HRID 1497547Notes

Reaction equation

HRID 1497547 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]([OH:12])=[O:11])=[CH:7][C:6]=2[CH:13]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:26](O)([CH3:29])([CH3:28])[CH3:27].N12CCCN=C1CCCCC2>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]([O:12][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:11])=[CH:7][C:6]=2[CH:13]=1

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 6059875-Methyl-1-benzothiophene-2-carboxylic acid

Product 1

HCID 90281979HCID 90281979, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-methyl-1-benzothiophene-2-carboxylic acid (1.50 g) in N,N-dimethylformamide (10.5 mL) was added 1,1′-carbonyldiimidazole (1.27 g), followed by stirring at room temperature for 2.5 hours. Subsequently, tert-butyl alcohol (1.44 mL) and 1,8-diazabicyclo[5.4.0]undeca-7-ene (1.17 mL) were added thereto, followed by heating at 50° C. for 24 hours. To the reaction mixture was added ethyl acetate, and the organic layer was washed with 1 M hydrochloric acid and a saturated aqueous sodium chloride solution in this order, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl 5-methyl-1-benzothiophene-2-carboxylate (1.78 g).

Workup

  1. temperatureby heating at 50° C. for 24 hours
  2. washthe organic layer was washed with 1 M hydrochloric acid
  3. concentrationa saturated aqueous sodium chloride solution in this order, and then concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-499ec77f23d144359c9c8faa7dd683ad
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

Loading…