HCID 67095383, compound → HCID 67095554, compound

HRID 390423Notes

Reaction equation

HRID 390423 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:26])(=[O:25])[NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([C:21]([F:24])([F:23])[F:22])[CH:13]=2)=[CH:6][CH:5]=1>C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>[OH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([C:21]([F:24])([F:22])[F:23])[CH:13]=2)(=[O:26])=[O:25])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 67095383HCID 67095383, compound

Product 1

HCID 67095554HCID 67095554, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226445Aluminium lithium hydrideSolvent

Procedure

To a solution of compound iii (3.26 g, 8.06 mmol) in dry THF (50 mL), LAH pallet (0.46 g, 12.10 mmol) was added at 0° C. The resulting reaction mixture was stirred for 4 h, quenched by the addition of water (5 mL), concentrated, diluted with ethyl acetate (50 mL), and washed, in tandem, with 1N HCl, water, 10% Na2CO3 aqueous solution, and brine. The organic layer was dried, filtered, and concentrated. The residue was purified by silica gel chromatography (ethyl acetate-hexane, 3:7) to afford 4-hydroxymethyl-N-(4-nitro-3-trifluoromethyl-phenyl)-benzenesulfonamide (iv) as light yellow solid with 71% yield. 1H NMR (300 MHz, CDCl3) δ 2.06 (br, 1H), 4.75 (s, 2H), 6.96 (br, 1H), 7.59 (d, J=10.17 Hz, 2H), 7.84 (d, J=8.19 Hz, 2H), 7.88 (d, J=8.43 Hz, 1H), 8.03 (d, J=8.43 Hz, 1H), 8.16 (s, 1H).

Workup

  1. customThe resulting reaction mixture
  2. customquenched by the addition of water (5 mL)
  3. concentrationconcentrated
  4. additiondiluted with ethyl acetate (50 mL)
  5. washwashed, in tandem, with 1N HCl, water, 10% Na2CO3 aqueous solution, and brine
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (ethyl acetate-hexane, 3:7)

Sources & evidence

ORD record
ord-76bc0383d95441f9a1a8709d42f41f45
Source dataset
uspto-grants-2013_02
Patent number
US08383656B2

Reaction notes

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