Ammonium Chloride → HCID 54543787, compound

HRID 1886197Notes

Reaction equation

HRID 1886197 reaction equation
COP([CH:7]([CH:13]([CH3:15])[CH3:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])(OC)=O.C([Li])CCC.[CH3:21][C:22](=[CH:24][CH2:25][CH2:26]/[C:27](=[CH:29]/[CH:30]=O)/[CH3:28])[CH3:23].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH3:14][CH:13]([C:7](=[CH:30][CH:29]=[C:27]([CH3:28])[CH2:26][CH2:25][CH:24]=[C:22]([CH3:23])[CH3:21])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:15]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 638011CitralHCID 19877457HCID 19877457, compoundHCID 178418339Butyllithium

Product 1

HCID 54543787HCID 54543787, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×

Procedure

To a solution of ethyl 2-(dimethylphosphono)-3-methylbutyrate (11.0 g, 41.3 mmol) in tetrahydrofuran (50 ml) chilled at -68° C. was dropwise added 1.62M solution of n-butyllithium in hexane (21.6 ml, 35.0 mmol) with stirring in 15 minutes under argon atmosphere. After stirring at -72° C. for 15 minutes, the mixture was mixed with geranial (4.0 g, 26.3 mmol), warmed up to room temperature in 30 minutes and stirred for 5 hours. The reaction mixture was chilled on an ice bath and mixed with saturated aqueous ammonium chloride (100 ml) and hexane (100 ml). The organic layer was separated, washed with saturated aqueous sodium chloride (50 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The resulting residue was chromatographed on a silica gel column (Eluent: n-hexane:ether=30:1) to give ethyl 2-(1-methylethyl)-5,9-dimethyl-2,4,8-decatrienate (3,07 g, 48%).

Workup

  1. stirringAfter stirring at -72° C. for 15 minutes
  2. stirringstirred for 5 hours
  3. temperatureThe reaction mixture was chilled on an ice bath
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous sodium chloride (50 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto remove the solvent
  9. customThe resulting residue was chromatographed on a silica gel column (Eluent: n-hexane:ether=30:1)

Sources & evidence

ORD record
ord-442c0500135741c68c341dd6b277706d
Source dataset
uspto-grants-1992_09
Patent number
US05149843

Reaction notes

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