Tetrahydrofuran → 4-formyl-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide

HRID 1434686Notes

Reaction equation

HRID 1434686 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:18][O:19][CH3:20])[C:13]2[S:14][CH:15]=[CH:16][N:17]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#N.CC(C[AlH]CC(C)C)C.C1C[O:33]CC1>>[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:18][O:19][CH3:20])[C:13]2[S:14][CH:15]=[CH:16][N:17]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)=[O:33]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 670014474-cyano-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide

Product 1

HCID 866116984-formyl-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide

Procedure

To a solution of 4-cyano-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide (4.5 mmol) in THF (50 mL) at −78° C. under argon was added DIBAL (5.0 mmol, 1M in THF) and the solution was allowed to warm to room temperature overnight. After the reaction was quenched with potassium sodium tartrate solution slowly, the mixture was extracted with ethyl acetate, and the organic phase was washed with brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by column chromatography to give 4-formyl-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide (3.1 mmol).

Workup

  1. customAfter the reaction was quenched with potassium sodium tartrate solution slowly
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-4e86e9d649ac4eaa8a9e6e11f3445233
Source dataset
uspto-grants-2009_11
Patent number
US07615569B2

Reaction notes

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