Toluene → HCID 131721140, compound

HRID 1417755Notes

Reaction equation

HRID 1417755 reaction equation
[C:1]12([C:11]3[CH:31]=[CH:30][C:14]([C:15]([NH:17][C:18]4[CH:29]=[CH:28][C:21]([C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])=[CH:20][CH:19]=4)=O)=[CH:13][C:12]=3[O:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C1(C)C=CC=CC=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:55])=CC=1>O>[C:1]12([C:11]3[CH:31]=[CH:30][C:14]([C:15]([NH:17][C:18]4[CH:29]=[CH:28][C:21]([C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])=[CH:20][CH:19]=4)=[S:55])=[CH:13][C:12]=3[O:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

5

Reactant 3

HCID 1140TolueneHCID 87949Lawesson's reagentHCID 67572951HCID 67572951, compound

Product 1

HCID 131721140HCID 131721140, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.9 g (5.6 mmol) of allyl 4-[4-(1-adamantyl)-3-methoxyethoxymethoxybenzamido]benzoate and 30 ml of toluene were introduced into a round-bottomed flask and 1.14 g (2.8 mmol) of Lawesson's reagent were added. The reaction medium was heated at reflux for three hours and was then evaporated to dryness. The residue obtained was taken up in water and dichloromethane and the organic phase was separated out after settling had taken place, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a column of silica, eluted with a mixture of heptane and ethyl acetate (80/20). After evaporation of the solvents, 1 g (33%) of the expected allylic ester was collected in the form of an orange-coloured oil.

Workup

  1. temperatureThe reaction medium was heated
  2. temperatureat reflux for three hours
  3. customwas then evaporated to dryness
  4. customThe residue obtained
  5. customdichloromethane and the organic phase was separated out
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue obtained
  9. customwas purified by chromatography on a column of silica
  10. washeluted with a mixture of heptane and ethyl acetate (80/20)
  11. customAfter evaporation of the solvents, 1 g (33%) of the expected allylic ester
  12. customwas collected in the form of an orange-coloured oil

Sources & evidence

ORD record
ord-9883f0e6d519477aa72083558a8d6dbc
Source dataset
uspto-grants-1999_03
Patent number
US05877342

Reaction notes

Loading…