Hexane → HCID 11253747, compound

HRID 389007Notes

Reaction equation

HRID 389007 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12]([C:15](OC)=[O:16])=[CH:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Li+].[BH4-].CCCCCC.C(OCC)(=O)C>C1COCC1>[C:1]1([CH3:19])[CH:2]=[CH:3][C:4]([S:7]([N:10]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11]2)(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 15304777Methyl 1-(4-methylbenzene-1-sulfonyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 11253747HCID 11253747, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10 (15.6 g, 0.063 mol) in 250 mL anhydrous THF was added LiBH4 (1.8 g, 0.08 mol) at 60° C. water bath for 24 h. The reaction was quenched by the addition of 1 M H2SO4 solution. The resulting solution was extracted with dichloromethane. The extracts were washed with saturated aqueous sodium bicarbonate, water and brine, dried over sodium sulphate, filtered and evaporated under vacuum to give light yellow solid which subjected to flash chromatography (silica gel, hexane:ethyl acetate=2:1) to afford 11 as a white solid (14.3 g, 90%). 1H NMR (CDCl3, δ/ppm), 7.74 (m, 2H), 7.29 (d, 2H), 7.12-7.09 (m, 2H), 6.29 (m, 1H), 4.46 (s, 2H), 2.39 (s, 3H), 1.86 (b, 1H).

Workup

  1. customThe reaction was quenched by the addition of 1 M H2SO4 solution
  2. extractionThe resulting solution was extracted with dichloromethane
  3. washThe extracts were washed with saturated aqueous sodium bicarbonate, water and brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customto give light yellow solid which

Sources & evidence

ORD record
ord-3e17e84787734de3b37ec09908b4f322
Source dataset
uspto-grants-2013_02
Patent number
US08378058B2

Reaction notes

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