Water → HCID 11805274, compound

HRID 2270458Notes

Reaction equation

HRID 2270458 reaction equation
[CH:1]([O:3][CH2:4][CH:5]([CH3:7])[CH3:6])=[CH2:2].[Cl:8][CH2:9][C:10](Cl)=[O:11].CN1CCOCC1.O>COC(C)(C)C>[Cl:8][CH:9]1[CH:1]([O:3][CH2:4][CH:5]([CH3:7])[CH3:6])[CH2:2][C:10]1=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 79724-MethylmorpholineHCID 7992Vinyl isobutyl ether

Product 1

HCID 11805274HCID 11805274, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

A solution formed by dissolving 30.0 g of isobutyl vinyl ether (0.3 mol) as the compound (V) and 34.9 g of chloroacetyl chloride (0.3 mol) as the compound (VI) in 135 ml of tert-butyl methyl ether was heated to 50˜55° C. with stirring. Subsequently, a solution formed by dissolving 30.3 g of N-methylmorpholine (with a pKa value of 7.4) (0.3 mol) in 45 ml of tert-butyl methyl ether was added dropwise to the aforementioned solution over two hours. Four hours after the completion of the dropwise addition, 40 ml of water was added thereto in order to separate the solution, followed by removal of the water layer. Analysis of the organic layer using gas chromatography under the following analysis conditions, revealed a yield of 75.8% for the compound (IV), 2-chloro-3-isobutoxycyclobutanone. Furthermore, after concentration of the aforementioned organic layer, a sample for analysis was obtained by means of distillation, and analyzed by means of elemental analysis and nuclear magnetic resonance analysis (NMR).

Workup

  1. customA solution formed
  2. temperaturewas heated to 50˜55° C.
  3. customSubsequently, a solution formed
  4. additionwas added dropwise to the aforementioned solution over two hours
  5. additionwas added
  6. customin order to separate the solution
  7. customfollowed by removal of the water layer
  8. customFurthermore, after concentration of the aforementioned organic layer, a sample for analysis was obtained by means of distillation

Sources & evidence

ORD record
ord-4f44b95e03c941678b181445968c301f
Source dataset
uspto-grants-2001_12
Patent number
US06331653B1

Reaction notes

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