Water → HCID 13533746, compound

HRID 1719827Notes

Reaction equation

HRID 1719827 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH2:5]([C:7]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH:8]=1)[CH3:6].O>CCOCC>[CH2:1]([C:10]1([OH:13])[CH2:11][CH2:12][C:7]([CH2:5][CH3:6])=[CH:8][CH2:9]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 13533745HCID 13533745, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 13533746HCID 13533746, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 35 ml of 3.2M ethereal ethyl magnesium bromide (Aldrich) in 75 ml of dry ether was added dropwise at gentle reflux a solution of 10.0 g of 4-ethyl-3-cyclohexen-1-one in 25 ml of ether. After one hour longer at reflux, the mixture was cooled and treated dropwise with 80 ml of water. The aqueous layer was extracted with ether and the combined ether layers was dried, concentrated, and Claisen-distilled to give 7.3 g of the desired product, b.p. 82°-86° C. (5 mm.).

Workup

  1. temperatureAfter one hour longer at reflux
  2. temperaturethe mixture was cooled
  3. extractionThe aqueous layer was extracted with ether
  4. dry with materialthe combined ether layers was dried
  5. concentrationconcentrated
  6. distillationClaisen-distilled

Sources & evidence

ORD record
ord-bc2cad4b399f45089ea1211b57349a1a
Source dataset
uspto-grants-1985_09
Patent number
US04542244

Reaction notes

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