Carbon Tetrachloride → HCID 18332479, compound

HRID 369124Notes

Reaction equation

HRID 369124 reaction equation
O[CH2:2][C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH:5]([C:8]1[O:12][N:11]=[C:10]([CH3:13])[CH:9]=1)[O:6][CH3:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:38]>C(#N)C>[Cl:38][CH2:2][C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH:5]([C:8]1[O:12][N:11]=[C:10]([CH3:13])[CH:9]=1)[O:6][CH3:7]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 18332478HCID 18332478, compound

Product 1

HCID 18332479HCID 18332479, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 1.24 g (5.3 mmol) of 5-(2-hydroxymethyl-α-methoxybenzyl)-3-methylisoxazole and 10 ml of acetonitrile was added 1.67 g (6.36 mmol) of triphenylphosphine and 1.23 ml (12.7 mmol) of carbon tetrachloride under ice-cooling and stirred at room temperature overnight. After completion of the reaction, the residue obtained by concentration under reduced pressure was purified by column chromatography on silica gel (ethyl acetate/n-hexane) to give 5-(2-chloromethyl-α-methoxybenzyl)-3-methylisoxazole (1.03 g, 77.2%) as colorless oil.

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. customthe residue obtained by concentration under reduced pressure
  4. customwas purified by column chromatography on silica gel (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-0f68f3e69f834d1194c44030341c9814
Source dataset
uspto-grants-2000_10
Patent number
US06136837

Reaction notes

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