HCID 20738654, compound → HCID 23512963, compound

HRID 354056Notes

Reaction equation

HRID 354056 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[C:9]2[O:13][CH:12]=[CH:11][C:10]=12)=O.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[OH:2][CH2:3][C:5]1[C:10]2[CH:11]=[CH:12][O:13][C:9]=2[C:8]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 20738654HCID 20738654, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 23512963HCID 23512963, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-methanesulfonylamino-benzofuran-4-carboxylic acid methyl ester (6.42 g, 23.8 mmole) in anhydrous tetrahydrofuran (155 mL) was added a solution of diisobutylaluminum hydride (1.5M solution in toluene, 80 mL, 120 mmole) slowly at 0° C. under nitrogen. The ice bath was removed and the reaction mixture was stirred at room temperature for three hours. Methanol (30 mL) was added slowly at 0° C. The reaction mixture was partitioned between ethyl acetate and 0.5 N hydrochloric acid. The organic extract was washed with brine, dried (anhydrous sodium sulfate), and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel eluting with 50 to 80% ethyl acetate in hexane to give N-(4-Hydroxymethyl-benzofuran-7-yl)-methanesulfonamide as a solid (5.64 g, 98%). 1H NMR (DMSO-d6) δ: 3.07 (s, 3H), 4.73 (d, 2H, J=5.70 Hz), 5.30 (t, 1H J=5.7 Hz), 7.10 (d, 1H, J=2.2 Hz), 7.21 (s, 2H), 8.05 (d, 1H, J=2.2 Hz), 9.78 (s, 1H). M−H 240.

Workup

  1. customThe ice bath was removed
  2. additionMethanol (30 mL) was added slowly at 0° C
  3. customThe reaction mixture was partitioned between ethyl acetate and 0.5 N hydrochloric acid
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried (anhydrous sodium sulfate)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash column chromatography over silica gel eluting with 50 to 80% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e71c38a1073b4aaab856f34410191a92
Source dataset
uspto-grants-2004_06
Patent number
US06756395B2

Reaction notes

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