Aluminium lithium hydride → HCID 86710159, compound

HRID 705383Notes

Reaction equation

HRID 705383 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N:21]([CH2:26][C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)[S:22]([CH3:25])(=[O:24])=[O:23])[C:18]([O:35][CH:36]([CH3:38])[CH3:37])=[CH:17][C:11]=3[C:12]=2[C:13](OC)=[O:14])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N:21]([CH2:26][C:27]4[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=4)[S:22]([CH3:25])(=[O:24])=[O:23])[C:18]([O:35][CH:36]([CH3:38])[CH3:37])=[CH:17][C:11]=3[C:12]=2[CH2:13][OH:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 89954963HCID 89954963, compound

Product 1

HCID 86710159HCID 86710159, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl 2-(4-fluorophenyl)-5-isopropoxy-6-(N-(4-methoxybenzyl)methylsulfonamido)benzofuran-3-carboxylate (0.8 g, 1.48 mmol) was dissolved in tetrahydrofuran cooled in an ice bath and treated with lithium aluminum hydride in tetrahydrofuran (1.0 M, 1.48 mL). The resulting solution was stirred at room temperature for 45 minutes. The reaction was quenched with 0.3 mL water, 0.3 mL 15% aqueous NaOH and 0.6 mL water, stirred 15 minutes, and decanted. The solid was washed with ethyl acetate, diluted with 100 mL ethyl acetate, and washed with 1 N aqueous H3PO, 10% aqueous sodium bicarbonate, and 10% aqueous sodium chloride. The mixture was dried over anhydrous sodium sulfate(s), filtered and the solvent was removed in vacuo leaving an oily residue, 0.68 g, 90%.

Workup

  1. temperaturecooled in an ice bath
  2. customThe reaction was quenched with 0.3 mL water, 0.3 mL 15% aqueous NaOH and 0.6 mL water
  3. stirringstirred 15 minutes
  4. customdecanted
  5. washThe solid was washed with ethyl acetate
  6. additiondiluted with 100 mL ethyl acetate
  7. washwashed with 1 N aqueous H3PO, 10% aqueous sodium bicarbonate, and 10% aqueous sodium chloride
  8. dry with materialThe mixture was dried over anhydrous sodium sulfate(s)
  9. filtrationfiltered
  10. customthe solvent was removed in vacuo
  11. customleaving an oily residue, 0.68 g, 90%

Sources & evidence

ORD record
ord-1c4aa1e09ce3469e8bb9f32c5cca44f2
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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