Triethylamine → 5-(Chloromethyl)-3-(propan-2-yl)-1,2-oxazole

HRID 2071069Notes

Reaction equation

HRID 2071069 reaction equation
[CH:1](=[N:5][OH:6])[CH:2]([CH3:4])[CH3:3].[CH2:7]([Cl:10])[C:8]#[CH:9].CCN(CC)CC.Cl([O-])=O.[Na+]>C(Cl)Cl>[Cl:10][CH2:7][C:8]1[O:6][N:5]=[C:1]([CH:2]([CH3:4])[CH3:3])[CH:9]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9023Propanal, 2-methyl-, oximeHCID 122213-Chloro-1-propyneHCID 23668197Sodium Chlorite

Product 1

HCID 123646025-(Chloromethyl)-3-(propan-2-yl)-1,2-oxazoleYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 1.0 g (11.5 mmol) of isobutyraldehyde oxime, 0.9 g (12.1 mmol) of propargyl chloride, and 0.7 mL (5.02 mmol) of Et3N in 30 mL of CH2Cl2 at 0° C. was added 125 mL of sodium chlorite solution (>4% chlorine). The ice bath was removed and stirring was continued with warming to r.t. After 1.5 h, CH2Cl2 was added, and the organic layer was washed with 20 mL of brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (10% EtOAc/hexanes) provided 1.14 g of 5-(chloromethyl)-3-isopropylisoxazole as a pale yellow liquid in about 62% yield. (60%)

Workup

  1. customThe ice bath was removed
  2. additionCH2Cl2 was added
  3. washthe organic layer was washed with 20 mL of brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash silica gel chromatography (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-56c5ea9e0d2c458998609f1b22e10d32
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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