Diethyl Ether → HCID 89738904, compound

HRID 1468251Notes

Reaction equation

HRID 1468251 reaction equation
[CH2:1]([C:3](=[CH2:6])[CH:4]=[O:5])[CH3:2].[CH:7]1([Mg]Cl)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C(OCC)C>[NH4+].[Cl-]>[CH:7]1([CH:4]([OH:5])[C:3](=[CH2:6])[CH2:1][CH3:2])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 70203EthylacroleinHCID 178478990HCID 178478990, compound

Product 1

HCID 89738904HCID 89738904, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

2-Ethylacroleine (25 g, 267 mmol) was added drop-wise to a 2 molar solution of cyclohexylmagnesium chloride in diethyl ether (167 ml, 334 mmol), at 0° C. under nitrogen. The reaction was then warmed up slowly to room temperature overnight. After cooling to 0° C., saturated aqueous NH4Cl (500 ml) was added slowly. The reaction was warmed up to room temperature and phases separated. The aqueous phase was re-extracted with diethyl ether. Each organic phase was washed with brine. Combined extracts were dried over sodium sulfate. The product was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 5:1) followed by bulb-to-bulb distillation (90-100° C./1 mbar). The product was obtained as colorless liquid (yield: 60%).

Workup

  1. customat 0° C.
  2. temperatureAfter cooling to 0° C.
  3. temperatureThe reaction was warmed up to room temperature
  4. customphases separated
  5. extractionThe aqueous phase was re-extracted with diethyl ether
  6. washEach organic phase was washed with brine
  7. dry with materialCombined extracts were dried over sodium sulfate
  8. customThe product was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 5:1)
  9. distillationfollowed by bulb-to-bulb distillation (90-100° C./1 mbar)

Sources & evidence

ORD record
ord-ee9b2d521e6e49e48cbd0fc8dc7e56a5
Source dataset
uspto-grants-2015_04
Patent number
US09000226B2

Reaction notes

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