HCID 10967505, compound → HCID 23356039, compound

HRID 233621Notes

Reaction equation

HRID 233621 reaction equation
[C:1]([CH:5]1[CH2:14][C:13]2[C:8](=[C:9]([O:17]C)[CH:10]=[CH:11][C:12]=2[O:15]C)[CH2:7][S:6]1)([O:3][CH3:4])=[O:2]>CC#N.O>[C:1]([CH:5]1[CH2:14][C:13]2[C:12](=[O:15])[CH:11]=[CH:10][C:9](=[O:17])[C:8]=2[CH2:7][S:6]1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 1

HCID 10967505HCID 10967505, compound

Product 1

HCID 23356039HCID 23356039, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of isothiochroman from step 1 above (253 mg, 0.94 mmol) in 3 ml of CH3CN was added dropwise a solution of ceric ammonium nitrate (1.550 g, 283 mmol) in 3 ml of H2O. The reaction mixture was stirred at 0° C. for 10 minutes and then at room temperature for 10 minutes, followed by extraction with CH2Cl2 (10 ml×3). The combined organic layers were washed with brine and water, dried over MgSO4, and then concentrated to a yellow residue (213 mg, 0.89 mmol) in 95% yield, which was found to be pure by H1NMR. 1H NMR (300 MHz, CDCl3) d:2.90 (m, 2H, HCHa,eCHC=O), 3.56 (m, 2H, HCHae--S), 3.73 (s, 3H, OCH3), 3.74 (s, 3H, OCH3), 3.75 (m, 1H, HC--S), 6.75 (m, 2H, ArH). 13C NMR (75.44 MHz, CDCl3) δ:22.2, 26.0, 37.4, 52.8, 136.2, 137.0, 140.0, 140.5, 172.0 (CO ester), 185.8, 187.0 (CO quinones). IR: (neat) 2956, 1736, 1658, 1607, 1442, 1409 cm-1.

Workup

  1. waitat room temperature for 10 minutes
  2. extractionfollowed by extraction with CH2Cl2 (10 ml×3)
  3. washThe combined organic layers were washed with brine and water
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-d262e332872c44ef9cbd43c376f08317
Source dataset
uspto-grants-1997_01
Patent number
US05593970

Reaction notes

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