HCID 10791478, compound → HCID 10679357, compound

HRID 1737301Notes

Reaction equation

HRID 1737301 reaction equation
[OH:1][C:2]([CH3:34])([CH3:33])[CH2:3][C:4]1[C:5]([CH2:22]SCC2C=CC(OC)=CC=2)=[C:6]([OH:21])[C:7]([CH2:10]SCC2C=CC(OC)=CC=2)=[CH:8][CH:9]=1>CCO>[OH:1][C:2]([CH3:34])([CH3:33])[CH2:3][C:4]1[C:5]([CH3:22])=[C:6]([OH:21])[C:7]([CH3:10])=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 10791478HCID 10791478, compound

Product 1

HCID 10679357HCID 10679357, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Raney nickel (RaNi, ca. 20 g) is washed five times with water and twice with anhydrous EtOH. A slurry of this catalyst in EtOH is then added to a solution of bis(sulfide) 37 (3.01 g, 6.04 mmol) in EtOH (30 mL). The resulting mixture is heated at vigorous reflux under N2 for 2 h, then cooled. The supernatant is decanted, and the catalyst is washed successively with MeOH and EtOAc (2×). The decanted organic layers are combined and evaporated. The residue is purified by FC (10:1, CH2Cl2 /iPrOH) to give 33 as a pale yellow oil (0.98 g, 84%) . 1H NMR (CDCl3) 6.94 (d, 1, J=7.7), 6.72 (d, 1, J=7.7), 2.81 (s, 2), 2.24 (s, 6), 1.24 (s, 6); 13C NMR (CDCl3) 152.44, 135.06, 127.42, 123.42, 122.91, 120.95, 71.59, 45.68, 29.41, 15.87, 12.76; MS (MW=194.3, CI/CH4, eE=70 eV) m/z 195 (M+H)+, 177 (base peak), 175, 149, 136, 91, 79.

Workup

  1. washRaney nickel (RaNi, ca. 20 g) is washed five times with water
  2. temperatureThe resulting mixture is heated
  3. temperatureat vigorous reflux under N2 for 2 h
  4. temperaturecooled
  5. customThe supernatant is decanted
  6. washthe catalyst is washed successively with MeOH and EtOAc (2×)
  7. customevaporated
  8. customThe residue is purified by FC (10:1, CH2Cl2 /iPrOH)

Sources & evidence

ORD record
ord-284930dc281e4d9d96ddf6016e336e40
Source dataset
uspto-grants-1999_10
Patent number
US05962469

Reaction notes

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