6-(But-3-en-1-yl)-3-ethoxycyclohex-2-en-1-one → 4-(But-3-en-1-yl)cyclohex-2-en-1-one

HRID 1758160Notes

Reaction equation

HRID 1758160 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([CH:11]1[C:16](=O)[CH:15]=[C:14]([O:18]CC)[CH2:13][CH2:12]1)[CH2:8][CH:9]=[CH2:10]>CCOCC>[CH2:7]([CH:11]1[CH2:16][CH2:15][C:14](=[O:18])[CH:13]=[CH:12]1)[CH2:8][CH:9]=[CH2:10]

Participants

4

Reactant 2

HCID 127883066-(But-3-en-1-yl)-3-ethoxycyclohex-2-en-1-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 127883074-(But-3-en-1-yl)cyclohex-2-en-1-oneYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a 0° C. slurry of 1.06 g. (26 mmoles) of lithium aluminum hydride in 75 ml. of ether was added a solution of 10 g. (51 mmoles) of 6-(3-butenyl)-3-ethoxy-2cyclohexen-1-one in 25 ml. of ether. After stirring for one hour, the reaction was quenched by addition of 100 ml. of 2 N hydrochloric acid. The quenched mixture was stirred for 30 minutes and then extracted with 300 ml. of ether. The ether extract was washed with 250 ml. saturated sodium bicarbonate, dried over magnesium sulfate and evaporated on a rotovapor. Distillation of the crude oil gave 5.98 g. (78%) of the title product.

Workup

  1. customTo a 0° C.
  2. customthe reaction was quenched by addition of 100 ml
  3. stirringThe quenched mixture was stirred for 30 minutes
  4. extractionextracted with 300 ml
  5. extractionThe ether extract
  6. washwas washed with 250 ml
  7. dry with materialsaturated sodium bicarbonate, dried over magnesium sulfate
  8. customevaporated on a rotovapor
  9. distillationDistillation of the crude oil
  10. customgave 5.98 g

Sources & evidence

ORD record
ord-41c79b40e25c42dcacf785cceb656e55
Source dataset
uspto-grants-1983_02
Patent number
US04371720

Reaction notes

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