Lawesson's reagent → HCID 19041796, compound

HRID 1684056Notes

Reaction equation

HRID 1684056 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH3:23][C@H:24]1[C@@:29]23[C:35]([O:36][C@H:27]([CH2:28]2)[CH2:26][C@@H:25]1[C:39]1[CH:40]=[CH:41][C:42]2[O:47][CH2:46][O:45][C:43]=2[CH:44]=1)=[CH:34][C:32](=O)[C:31]([O:37][CH3:38])=[CH:30]3>C1(C)C=CC=CC=1>[O:47]1[C:42]2[CH:41]=[CH:40][C:39]([CH:25]3[CH:24]([CH3:23])[C:29]45[CH2:28][CH:27]([O:36][C:35]4=[CH:34][C:32](=[S:10])[C:31]([O:37][CH3:38])=[CH:30]5)[CH2:26]3)=[CH:44][C:43]=2[O:45][CH2:46]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 9819306(2S,4S,5R,5aS)-4-(1,3-Benzodioxol-5-yl)-2,3,4,5-tetrahydro-7-methoxy-5-methyl-8H-2,5a-methano-1-benzoxepin-8-one

Product 1

HCID 19041796HCID 19041796, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Lawesson's reagent (119.3 mg, 0.3 mmoles) is added to a stirred solution of futoenone (200 mg, 0.59 mmoles) in toluene (4 ml). The reaction is heated to 60° C. in an oil bath for 2-3 h. TLC of the reaction mixture shows almost complete conversion of starting material. The reaction turns from a green to violet upon heating. The reaction is concentrated in vacuo and purified by MPLC on silica gel using ethyl acetate. A purple foam (154.2 mg, 73.5%) forms upon drying in vacuo. M+(CI)=357. 1H NMR ppm: 0.59 (3H, d), 1.72 (1H, t), 2.07 (1H, m), 2.21 (1H, d), 2.30 (1H, m), 2.43 (1H, m), 2.58 (1H, m), 3.71 (3H, s), 5.08 (1H, t), 5.46 (1H, s), 5.92 (2H, s), 6.65 (4H, m).

Workup

  1. temperatureupon heating
  2. concentrationThe reaction is concentrated in vacuo
  3. custompurified by MPLC on silica gel
  4. customupon drying in vacuo

Sources & evidence

ORD record
ord-11f74f12132540f48688b89372b376d1
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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