Water → HCID 66894542, compound

HRID 1162072Notes

Reaction equation

HRID 1162072 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[S:10]([C:13]1[CH:14]=[C:15]([C:22](OC)=[O:23])[C:16]2[O:20][CH:19]=[CH:18][C:17]=2[CH:21]=1)(=[O:12])=[O:11].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[S:10]([C:13]1[CH:14]=[C:15]([CH2:22][OH:23])[C:16]2[O:20][CH:19]=[CH:18][C:17]=2[CH:21]=1)(=[O:11])=[O:12]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66893431HCID 66893431, compound2×

Product 1

HCID 66894542HCID 66894542, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl 5-[(2-methoxy-5-methylphenyl)sulfonyl]-1-benzofuran-7-carboxylate (400 mg, 1.1 mmol; Intermediate 67) was dissolved in dry THF (3 mL) and 1 M lithium aluminiumhydride in THF (0.3 mL) was slowly added. The mixture was stirred at room temperature overnight. After this time, water (0.15 mL) was added and stirring was continued for 10 min, followed by the addition of 2 M aqueous NaOH (0.15 mL) and water (0.45 mL). The precipitate formed was filtered off and the solvent was evaporated. The crude product was used in the next step without further purification. MS (ESI+) for C17H16O5S m/z 333 (M+H)+.

Workup

  1. stirringstirring
  2. waitwas continued for 10 min
  3. customThe precipitate formed
  4. filtrationwas filtered off
  5. customthe solvent was evaporated
  6. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-034b53fada944bbb814215dfe471ddeb
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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