Ammonium Chloride → HCID 22630149, compound

HRID 2307087Notes

Reaction equation

HRID 2307087 reaction equation
[CH2:1]([Mg]Br)[CH:2]=[CH2:3].[CH2:6]([C:8]1([CH2:17][CH3:18])[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][C:10](=[O:16])[CH2:9]1)[CH3:7].[NH4+].[Cl-]>CCOCC>[CH2:3]([C:10]1([OH:16])[CH2:11][C:12]([CH3:14])([CH3:15])[CH2:13][C:8]([CH2:6][CH3:7])([CH2:17][CH3:18])[CH2:9]1)[CH:2]=[CH2:1]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10845166HCID 10845166, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 22630149HCID 22630149, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred 1 M etheral solution of allylmagnesium bromide (20 ml, 20 mmol) was added dropwise a solution of 3,3-diethyl-5,5-dimethylcyclohexanone (25) (1.47 g, 8.06 mmol) in dry ether (5 ml). The mixture was stirred for 1 h at ambient temperature and boiled at reflux for 10 min. Then it was cooled with ice water and treated with saturated aqueous NH4Cl (40 ml). The organic layer was separated and washed with water and brine. After drying over anhydrous MgSO4, the solution was concentrated in vacuo. The residue was purified by column chromatography on silica gel (light petroleum ether). A fraction with Rf 0.7 (Hexane:EtOAc, 13:2) was collected. Evaporation of the solvent afforded 26 (1.35 g, 74%) as a colorless oil. 1H NMR (CDCl3, TMS): 0.74 (6H, t, 7 Hz, 2CH3 of ethyl); 0.88 (3H, s, 5-CH3eq); 1.19 (3H, s, 5-CH3ax); 0.80-2.05 (10H, m, 2,4,6-CH2 and 2CH2 of ethyl); 2.14 (2H, d, 7 Hz, CH2C═); 4.95-5.30 (2H, m, ═CH2) and 5.65-6.20 ppm (1H, m, ═CH).

Workup

  1. temperatureat reflux for 10 min
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialAfter drying over anhydrous MgSO4
  5. concentrationthe solution was concentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (light petroleum ether)
  7. customA fraction with Rf 0.7 (Hexane:EtOAc, 13:2) was collected
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-264711b2d5fb467b990021e87fc62654
Source dataset
uspto-grants-2004_12
Patent number
US06828462B2

Reaction notes

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