Methanesulfonyl chloride → HCID 86673332, compound

HRID 571125Notes

Reaction equation

HRID 571125 reaction equation
[C:1]([O:5][C:6]([C:8]1[S:9][C:10]([CH:13]=O)=[CH:11][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].CS([Cl:21])(=O)=O.C(N(C(C)C)CC)(C)C>O1CCCC1.CO>[C:1]([O:5][C:6]([C:8]1[S:9][C:10]([CH2:13][Cl:21])=[CH:11][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 4311764Sodium borohydrideHCID 21473735tert-Butyl 5-formylthiophene-2-carboxylate

Product 1

HCID 86673332HCID 86673332, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-formyl-2-thiophencarboxylic acid tert-butyl ester (5g, 23.6mmol) in tetrahydrofuran (50 ml) and methanol (5 ml), was added sodium borohydride (0.50 g, 13.0 mmol) at 0° C., and the mixture was stirred for 2 hours at room temperature. The reaction mixture was partitioned between ethyl acetate and 0.5N-hydrochloric acid solution. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was dissolved in dichloromethane (100 mL), methanesulfonyl chloride (1.9 ml, 24mmol) and diisopropylethylamine (5.7 ml, 33 mmol) were added at 0° C., and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, 0.5N-hydrochloric acid solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound (5.3 g, 23 mmol).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and 0.5N-hydrochloric acid solution
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. dissolutionthe obtained residue was dissolved in dichloromethane (100 mL)
  7. stirringthe mixture was stirred at room temperature overnight
  8. customThe solvent was evaporated under reduced pressure, 0.5N-hydrochloric acid solution
  9. additionwas added to the residue
  10. extractionthe mixture was extracted with ethyl acetate
  11. washThe extract was washed with brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-22d7e479c3104b5691cf40c88e653885
Source dataset
uspto-grants-2015_05
Patent number
US09024044B2

Reaction notes

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