Thiophenol → HCID 131736280, compound

HRID 1053514Notes

Reaction equation

HRID 1053514 reaction equation
N12CCN(CC1)CC2.[C:9]1([SH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:16]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)(=[O:19])[C:17]#[CH:18].[OH-].[Na+]>C1COCC1>[C:9]1([S:15][CH:18]=[CH:17][C:16]([O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)=[O:19])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 9237DabcoHCID 14798Sodium HydroxideHCID 10560973HCID 10560973, compound

Product 1

HCID 131736280HCID 131736280, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1,4-diazabicyclo[2.2.2]octane (DABCO, 10 mg, 0.89 mmol) and thiophenol (99 mg, 0.89 mmol) in dry THF (20 mL) at RT was added compound 1 (200 mg, 0.89) dissolved in dry THF (2 mL) through a syringe over 12 min. The reaction mixture was further stirred for 20 min. 10% NaOH(aq) was added. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed by evaporation. The crude product was purified by column chromatography using ethyl acetate:hexane (2:8) as an eluent to give compound 4 (254 mg, 85%). 1H NMR (400 MHz, CDCl3) δ 5.84 (d, J=15.0 Hz, 1H), 7.18 (d, J=8.6 Hz, 2H), 7.46 (m, 6H), 7.58 (m, 6H), 8.05 (d, J=15.0 Hz, 1H). HRMS ESI (m/z): Calculated for C21H16O2S ([M+H]+): 333.0871. found: 333.0852.

Workup

  1. washThe combined organic layer was washed with brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed by evaporation
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-8a43e9d4c685497e96d97330ced86ffe
Source dataset
uspto-grants-2016_07
Patent number
US09393306B2

Reaction notes

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