Potassium Carbonate → 5-[4-(Sec-butyloxy)-phenoxymethyl]-3-methylisoxazole

HRID 2050620ノート

反応式

HRID 2050620 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH:7]([O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)([CH2:9][CH3:10])[CH3:8].Cl[CH2:20][C:21]1[O:25][N:24]=[C:23]([CH3:26])[CH:22]=1>CN(C)C=O>[CH:7]([O:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:20][C:21]2[O:25][N:24]=[C:23]([CH3:26])[CH:22]=2)=[CH:16][CH:17]=1)([CH2:9][CH3:10])[CH3:8]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 71314965-(Chloromethyl)-3-methyl-1,2-oxazoleHCID 138820044-(1-Methyl-1-propyloxy)-phenol

生成物 1

HCID 146501035-[4-(Sec-butyloxy)-phenoxymethyl]-3-methylisoxazole収率 85.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

4.6 g of anhydrous potassium carbonate is added to 5.0 g of 4-sec-butyloxyphenol in 80 ml of absolute dimethylformamide, and the mixture is stirred for one hour at 80° C. At this temperature, 3.9 g of 5-chloromethyl-3-methylisoxazole is dripped in and the mixture is stirred for a further seven hours at 90° C. The batch is then stirred into 300 ml of ice water, extracted three times, each time with 100 ml of methyl tert-butyl ether and the organic phase is washed twice with 2N sodium hydroxide solution (50 ml in each instance) and then three times with water (50 ml in each instance). Drying over sodium sulfate and removal of the solvent under reduced pressure give 6.6 g of 5-[4-(sec-butyloxy)-phenoxymethyl]-3-methylisoxazole, which is obtained, after chromatography over silica gel using toluene/ethyl acetate(1:1) as eluant, as a viscous oil. According to 1H-NMR spectroscopy, the oil is pure.

後処理

  1. stirringis stirred for a further seven hours at 90° C
  2. extractionextracted three times
  3. washeach time with 100 ml of methyl tert-butyl ether and the organic phase is washed twice with 2N sodium hydroxide solution (50 ml in each instance) and then three times with water (50 ml in each instance)
  4. dry with materialDrying over sodium sulfate and removal of the solvent under reduced pressure

出典と根拠

ORDレコード
ord-029cf784e1174bb0a1149c40385dcb56
出典データセット
uspto-grants-1991_05
特許番号
US05013847

反応ノート

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