Water → HCID 13533746, compound

HRID 1154059Notes

Reaction equation

HRID 1154059 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 were 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 were dried
  5. concentrationconcentrated
  6. distillationClaisen-distilled

Sources & evidence

ORD record
ord-e5de98912d1644a8aed290a18626275d
Source dataset
uspto-grants-1984_12
Patent number
US04487945

Reaction notes

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