3-Chloro-2-methyl-1-propene → HCID 57002668, compound

HRID 365507Notes

Reaction equation

HRID 365507 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([O:9][CH2:10][CH3:11])([OH:8])[CH3:7])[CH3:4].[CH2:12](Cl)[C:13](=[CH2:15])[CH3:14]>C1COCC1>[CH2:12]([O:8][C:6]([O:9][CH2:10][CH3:11])([O:5][CH2:3][CH3:4])[CH3:7])[C:13](=[CH2:15])[CH3:14]

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 24758Sodium hydrideHCID 22028210HCID 22028210, compound

Product 1

HCID 57002668HCID 57002668, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold (0° C.) suspension of NaH (2.68 g, 60%) in THF (150 mL) was added a solution of 1,1-diethoxyethanol [which was prepared according to the literature procedure of Zirkle, C. L. et. al. J. Org. Chem. 1961, 26, 395-407] (9.00 g) in THF (20 mL), and the reaction mixture was stirred at room temperature for 1 hour before adding methallyl chloride (8.0 mL). The reaction mixture was heated to reflux overnight, cooled and filtered through a plug of celite. Solvent was removed by rotary evaporation, and the residue purified by column chromatography (silica, 20% ether/hexane) to give 1,1-diethoxyethyl methallyl ether (11.5, 90%). Ozonolysis of a chilled (-30° C.) solution of this ether (6.00 g) in EtOAc (80 mL) was carried out until no starting material was detectable by TLC (1 hour). At this time, the reaction was purged with oxygen, treated with Pd(OH)2 (150 mg) and stirred under an atmosphere of hydrogen overnight. The catalyst was filtered away, and the filtrate was concentrated by rotary evaporation. The resulting residue was purified by column chromatography (silica, 20% EtOAc/hexane) to afford the title compound (4.53 g, 82%).

Workup

  1. customwas prepared
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux overnight
  4. temperaturecooled
  5. filtrationfiltered through a plug of celite
  6. customSolvent was removed by rotary evaporation
  7. customthe residue purified by column chromatography (silica, 20% ether/hexane)

Sources & evidence

ORD record
ord-75b968b04b01459b82b41fe2c20192b9
Source dataset
uspto-grants-2000_10
Patent number
US06127401

Reaction notes

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