Methyl chloroformate → HCID 18424408, compound

HRID 1282440Notes

Reaction equation

HRID 1282440 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([CH2:15][F:16])([C:13]#[CH:14])[CH2:11][F:12])=[CH:5][CH:4]=1.CCCCCC.C([Li])CCC.Cl[C:31]([O:33][CH3:34])=[O:32]>C(OCC)C>[F:16][CH2:15][C:10]([CH2:11][F:12])([O:9][C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:17])([F:18])[F:1])=[CH:4][CH:5]=1)[C:13]#[C:14][C:31]([O:33][CH3:34])=[O:32]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 8058Hexane2×HCID 184244041-Fluoro-2-fluoromethyl-3-butyn-2-yl 4-trifluoromethylphenyl etherHCID 178418339Butyllithium

Product 1

HCID 18424408HCID 18424408, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

An amount (0.53 g) of 1-fluoro-2-fluoromethyl-3-butyn-2-yl 4-trifluoromethylphenyl ether was dissolved in diethyl ether (3 ml); to the solution under cooling with ice, a hexane solution (1.4 ml) of 1.69 M n-butyllithium was added dropwise under a nitrogen atmosphere. After the end of the dropwise addition, the mixture was stirred for 1 hour under cooling with ice. The resulting mixture was added dropwise to a solution of methyl chloroformate (0.38 g) in diethyl ether (3 ml) under a nitrogen atmosphere under cooling with ice. After stirring the mixture for 1 hour under cooling with ice, hexane was added, followed by washing with water and a saturated aqueous solution of sodium chloride. The mixture was dried with anhydrous sodium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluent; hexane/methylene chloride=1/1) to give the titled compound (0.51 g).

Workup

  1. temperatureto the solution under cooling with ice
  2. additionAfter the end of the dropwise addition
  3. temperatureunder cooling with ice
  4. temperatureunder cooling with ice
  5. stirringAfter stirring the mixture for 1 hour
  6. additionwas added
  7. washby washing with water
  8. dry with materialThe mixture was dried with anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-133c30eca0d74808a8f5d9368ba32755
Source dataset
uspto-grants-2002_09
Patent number
US06455708B1

Reaction notes

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