1,4-Dioxaspiro[4.5]decan-8-one → HCID 19705234, compound

HRID 727182Notes

Reaction equation

HRID 727182 reaction equation
[Br:1][C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)([CH3:4])[CH3:3].[Mg].C1O[C:16]2([CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]2)[O:15]C1>O1CCCC1>[Br:1][C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)([CH3:4])[CH3:3].[Cl:11][C:7]1[CH:6]=[C:5]([C:2]([C:19]2[CH2:20][CH2:21][C:16](=[O:15])[CH2:17][CH:18]=2)([CH3:4])[CH3:3])[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5462224MagnesiumHCID 19705234HCID 19705234, compound

Product 2

HCID 19705234HCID 19705234, compoundHCID 19705279HCID 19705279, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

The Grignard reagent of 2-bromo-2-(3-chlorophenyl)propane is prepared by adding dropwise a solution of 9.3 grams (0.040 mole) of 2-bromo-2-(3-chlorophenyl)propane in 45 mL of dry tetrahydrofuran to 1.1 grams (0.044 mole) of magnesium turnings in 25 mL of refluxing tetrahydrofuran. Upon completion of addition, the Grignard reagent is stirred at reflux for one hour. The reaction mixture is then cooled in an ice-water bath, and a solution of 6.2 grams (0.040 mole) of 1,4-cyclohexanedione mono-ethylene ketal in about 25 mL of tetrahydrofuran is added dropwise. Upon completion of addition, the reaction mixture is allowed to warm to ambient temperature where it is stirred for about 18 hours. After this time the reaction is quenched by the addition of 100 mL of aqueous 10% hydrochloric acid. The reaction mixture is stirred for 10 minutes and then is extracted with two 50 mL portions of diethyl ether. The combined extracts are washed with 10 mL of water and then are dried with magnesium sulfate. The mixture is filtered and concentrated under reduced pressure, yielding 1-[2-(3-chlorophenyl)propan-2-yl]-1-cyclohexen-4-one.

Workup

  1. additionUpon completion of addition
  2. temperatureat reflux for one hour
  3. temperatureThe reaction mixture is then cooled in an ice-water bath
  4. additionUpon completion of addition
  5. customAfter this time the reaction is quenched by the addition of 100 mL of aqueous 10% hydrochloric acid
  6. stirringThe reaction mixture is stirred for 10 minutes
  7. extractionis extracted with two 50 mL portions of diethyl ether
  8. washThe combined extracts are washed with 10 mL of water
  9. dry with materialare dried with magnesium sulfate
  10. filtrationThe mixture is filtered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ada06743b52141189b1e677c612bae07
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Reaction notes

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