Triethylamine → HCID 543456, compound

HRID 894408Notes

Reaction equation

HRID 894408 reaction equation
[C:1]1([CH:7]([SeH])[CH:8]([CH2:15]C)[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])C=CC=CC=1.ClC1C=CC=C(C(OO)=O)C=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:7]([C:8](=[CH2:15])[CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 131712314HCID 131712314, compound

Product 1

HCID 543456HCID 543456, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of selenide XIII (1.8 g, 6.0 mmol) in methylene chloride (15 ml) at -78° C. was added m-chloroperbenzoic acid (1.28 g, 85%, 6.3 mmol). The solution was allowed to warm to room temperature over 30 min. and was then washed with water, saturated sodium carbonate and dried (MgSO4). The methylene chloride was removed in vacuo and the selenoxide was taken up in carbon tetrachloride (15 ml). Triethylamine (640 mg, 6.3 mmol) was added and the solution was refluxed under nitrogen for 2 h. The reaction was taken up in methylene chloride (25 ml), washed with saturated aqueous sodium bicarbonate, dried (MgSO4) and concentrated on a roto-evaporator. The crude olefin XIV was distilled bp 70°-75° C. (25 mm) to give a colorless oil (630 mg, 74%).

Workup

  1. washwas then washed with water, saturated sodium carbonate
  2. dry with materialdried (MgSO4)
  3. customThe methylene chloride was removed in vacuo
  4. temperaturethe solution was refluxed under nitrogen for 2 h
  5. washwashed with saturated aqueous sodium bicarbonate
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated on a roto-evaporator
  8. distillationThe crude olefin XIV was distilled bp 70°-75° C. (25 mm)

Sources & evidence

ORD record
ord-853bf539682947f092db13150109d0ff
Source dataset
uspto-grants-1981_08
Patent number
US04283536

Reaction notes

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