Water → HCID 54388607, compound

HRID 1252461Notes

Reaction equation

HRID 1252461 reaction equation
[CH3:1][CH:2]1[O:7][CH:6]([CH3:8])[CH2:5][NH:4][CH2:3]1.[CH2:9]([C:13]1[S:17][C:16]([CH:18]2[CH2:20][CH:19]2[C:21](Cl)=[O:22])=[CH:15][CH:14]=1)[CH2:10][CH2:11][CH3:12].O>[Na]>[CH2:9]([C:13]1[S:17][C:16]([CH:18]2[CH2:20][CH:19]2[C:21]([N:4]2[CH2:5][CH:6]([CH3:8])[O:7][CH:2]([CH3:1])[CH2:3]2)=[O:22])=[CH:15][CH:14]=1)[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 1108622,6-DimethylmorpholineHCID 20139949HCID 20139949, compound

Product 1

HCID 54388607HCID 54388607, compound

Reagents, catalysts & solvents 1

HCID 5360545SodiumSolvent

Conditions

Temperature
20 °C

Procedure

2,6-Dimethylmorpholine (5.0 g, 0.043 mol) was added dropwise to a solution of 2-(5-n-butylthiophen-2-yl)-cyclopropanecarbonyl chloride (4.85 g, 0.02 mol) in sodium dried ether (40 ml) at 10° C. and after complete addition the solution was stirred at 20° C. for 3 hours. The reaction mixture was poured into water and extracted with diethyl ether (2×100 ml). The ethereal extracts were washed with water, dried over anhydrous sodium sulphate, and the solvent removed to give 2-(5-n-butylthiophen-2-yl)-cyclopropanecarbonyl-2,6-dimethylmorpholine (5.8 g, 90% as a yellow oil. A solution of 2-(5-n-butylthiophen-2-yl)-chclopropanecarbonyl-2,6-dimethylmorpholine (5.8 g, 0.018 mol) in sodium dried ether (30 ml) was added dropwise to a suspension of lithium aluminium hydride (0.8 g, 0.02 mol) in sodium dried ether (20 ml) and the reaction mixture stirred at room temperature for 3 hours. The reaction mixture was poured carefully into water and extracted with diethyl ether. The ethereal extracts were washed with water, dried over anhydrous sodium sulphate, and the solvent removed to give a colourless oil. This oil was purified by column chromatography (silica eluted with ethyl acetate/petroleum ether 2:3) to give the title compound (1.3 g, 24%).

Workup

  1. additionafter complete addition the solution
  2. extractionextracted with diethyl ether (2×100 ml)
  3. washThe ethereal extracts were washed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customthe solvent removed

Sources & evidence

ORD record
ord-20b0bc4988d64ccc9d9b1212140b886f
Source dataset
uspto-grants-1988_05
Patent number
US04743602

Reaction notes

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