Benzyl chloroformate → HCID 23497522, compound

HRID 1837081Notes

Reaction equation

HRID 1837081 reaction equation
[CH2:1]([O:3][CH:4]([O:6][CH2:7][CH2:8][C:9]#[CH:10])[CH3:5])[CH3:2].C([Li])CCC.Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>O1CCCC1>[CH2:1]([O:3][CH:4]([O:6][CH2:7][CH2:8][C:9]#[C:10][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 131717324-(1-Ethoxyethoxy)-1-butyneHCID 178418339Butyllithium

Product 1

HCID 23497522HCID 23497522, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The product from Example 31A (79.99 g, 0.563 mole) in tetrahydrofuran (1 L) was treated dropwise at −78° C. with n-butyllithium (2.5 M in hexane, 0.563 mole, 225 mL). The reaction mixture was stirred at −78° C. for 30 minutes and then benzyl chloroformate (0.563 mole, 80.4 mL) was added dropwise. The reaction mixture was stirred at −78° C. for 2 hours, allowed to warm to ambient temperature and stirred overnight. After quenching with water, ethyl acetate was added and the layers were separated. The organic layer was dried over magnesium sulfate, filtered and concentrated. Flash chromatography of the residue (silica, hexane to hexane:ethyl acetate, 30:1 to 4:1) provided the title compound as a colorless oil (155.5 g, 78%).

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for 2 hours
  2. temperatureto warm to ambient temperature
  3. stirringstirred overnight
  4. customAfter quenching with water, ethyl acetate
  5. additionwas added
  6. customthe layers were separated
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-bca14c13d81145fbbc3a7ea5099a2f79
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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