4-Toluenesulfonyl chloride → HCID 12041750, compound

HRID 1263621Notes

Reaction equation

HRID 1263621 reaction equation
[OH:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]2[C:5]([C:6](=[O:20])[CH:7]=[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[O:9]2)=[CH:4][CH:3]=1.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[CH2:18]([O:17][C:15]([C:8]1[O:9][C:10]2[C:5]([C:6](=[O:20])[CH:7]=1)=[CH:4][CH:3]=[C:2]([O:1][S:27]([C:24]1[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=1)(=[O:29])=[O:28])[C:11]=2[N+:12]([O-:14])=[O:13])=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 624330HCID 624330, compound

Product 1

HCID 12041750HCID 12041750, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 7-hydroxy-8-nitro-4-oxochromen-2-carboxylate [J.Chem. Soc. (c), 1970, 2609] ( (5.58 g, 0.02 mol) in anhydrous THF (100 mL) was added p-toluenesulfonyl chloride (7.63 g, 0.04 mol) and K2CO3 (5.52 g, 0.04 mol). The reaction mixture was allowed to stir for 12 hours at room temperature. The solution was filtered, and the filtrate was diluted with EtOAc (200 mL) and washed sequentially with saturated NaHCO3 solution (30 mL) and water (2×30 mL), dried over anhydrous Na2SO4, and filtered. The solvent evaporated to give a white solid which was recrystallized from EtOAc-hexane (1:1) to give 8.15 g (94%) of the title compound: mp 125° C.; 1H NMR (400 MHz, CDCl3): 1.39 (t, J=7Hz, 3H), 2.48, (s, 3H), 4.42 (q, J=7.0 Hz, 2H), 7.14 (s, 1H), 7.38 (d, J=9 Hz, 1H), 7.67 (d, J=9 Hz, 1H), 7.80 (d, J=9 Hz, 2H), 8.33 (d, J=9 Hz); IR: 3450, 3080, 2980, 1740, 1670, 1610, 1540, 1490, 1230 cm−1; MS 451[M+NH4].

Workup

  1. filtrationThe solution was filtered
  2. additionthe filtrate was diluted with EtOAc (200 mL)
  3. washwashed sequentially with saturated NaHCO3 solution (30 mL) and water (2×30 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customThe solvent evaporated
  7. customto give a white solid which
  8. customwas recrystallized from EtOAc-hexane (1:1)

Sources & evidence

ORD record
ord-fb6415a4bd3a44ca9e1fb6b5cb5e7607
Source dataset
uspto-grants-2003_04
Patent number
US06541501B2

Reaction notes

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