Ethyl Acetate → HCID 24960169, compound

HRID 1925096Notes

Reaction equation

HRID 1925096 reaction equation
FC(F)(F)S(O[C:7]1C2COCC3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[C:17]=3[C:11]=2[CH:10]=[CH:9][C:8]=1[O:28][CH3:29])(=O)=O.O.[SH-:33].[Na+].[C:35]([O:38][CH2:39][CH3:40])(=O)[CH3:36]>N1CCCC1=O>[CH3:29][O:28][C:8]1[CH:9]=[CH:10][C:11]2[C:17]3[C:18]([O:26][CH3:27])=[C:19]([O:24][CH3:25])[C:20]([O:22][CH3:23])=[CH:21][C:40]=3[CH2:39][O:38][CH2:35][C:36]=2[C:7]=1[SH:33]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 16211346Sodium hydrosulfide hydrateHCID 24959805HCID 24959805, compound

Product 1

HCID 24960169HCID 24960169, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 120252-PyrrolidoneCatalyst

Conditions

Temperature
90 °C

Procedure

A mixture of 3,9,10,11-tetramethoxy-5,7-dihydrodibenzo[c,e]oxepin-4-yl trifluoromethanesulfonate (Example 7, 85.2 mg, 0.183 mmol), sodium hydrosulfide hydrate (41.7 mg, 0.743 mmol) and 2-pyrrolidinone (0.4 mL, 0.005 mmol) in a sealed tube was sonicated (Branson 1510, output 70 W) for a period of 10 minutes and then stirred at an oil bath temperature of 90° C. for 1 hour, which afforded a pungent yellow solid. Column chromatography (petroleum ether 60-80°—ethyl acetate 1:1) gave the title compound as a yellow gum (50 mg, 78%); νmax/cm−1 (thin film) 2942, 2867, 2545, 1595, 1486; NMR Spectrum δH (400 MHz, CDCl3) 3.76 (3H, s, OCH3), 3.85 (1H, d, J 12.6 Hz, 5-H or 7-H), 3.92 (3H, s, OCH3), 3.94 (3H, s, OCH3), 3.96 (3H, s, OCH3), 4.05 (1H, d, J 12.6 Hz, 5-H or 7-H), 4.40 (1H, d, J 11.9 Hz, 5-H or 7-H), 5.15 (1H, d, J 11.9 Hz, 5-H or 7-H), 5.86 (1H, s, SH), 6.78 (1H, m, 8-H), 6.94 (1H, d, J 8.5 Hz, 2-H), 7.21 (1H, d, J 8.5 Hz, 1-H); NMR Spectrum δC (100 MHz, CDCl3) 56.44, 56.52, 59.65, 61.23, 61.52, 68.23, 109.17, 110.36, 121.23, 121.49, 126.85, 131.06, 131.56, 143.05, 143.80, 145.96, 151.07, 153.14; m/z (CI, NH3) no molecular ion; Rf (petroleum ether 60-80°—ethyl acetate 1:1) 0.32.

Workup

  1. customwas sonicated (Branson 1510, output 70 W) for a period of 10 minutes
  2. customwhich afforded a pungent yellow solid

Sources & evidence

ORD record
ord-1617c1611f86494bb8741fd470a2c3b5
Source dataset
uspto-grants-2012_05
Patent number
US08178578B2

Reaction notes

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