4-Methyl-5-vinylthiazole → (E)-methyl 2-(cyclohexyloxy)-8-(4-methylthiazol-5-yl)oct-7-enoate

HRID 445404ノート

反応式

HRID 445404 の反応式
[CH:1]1([O:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18])[C:9]([O:11][CH3:12])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:19][C:20]1[N:21]=[CH:22][S:23][C:24]=1C=C>C1(C)C=CC=CC=1>[CH:1]1([O:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]/[C:24]2[S:23][CH:22]=[N:21][C:20]=2[CH3:19])[C:9]([O:11][CH3:12])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 156544-Methyl-5-vinylthiazoleHCID 66822373Methyl 2-(cyclohexyloxy)oct-7-enoate

生成物 1

HCID 66822185(E)-methyl 2-(cyclohexyloxy)-8-(4-methylthiazol-5-yl)oct-7-enoate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

A mixture of methyl 2-hydroxyoct-7-enoate (6.88 g, 0.040 mmol), dichloromethane (40 mL), 3,4-dihydro-2H-pyran (7.4 mL, 0.082 mol), and 6 drops of trifluoroacetic acid was stirred at room temperature overnight. The resulting mixture was concentrated in vacuo to yield methyl 2-(cyclohexyloxy)oct-7-enoate, which was used in the next step without further purification. A solution of methyl 2-(cyclohexyloxy)oct-7-enoate (500.0 mg, 1.95 mmol) dissolved in toluene (33 mL) containing 4-methyl-5-vinylthiazole (1.11 mL, 19.5 mmol) and Grubb's 2nd generation catalyst (166 mg, 0.195 mmol) was flushed with argon and heated in a sealed tube at 100° C. for 20 h. After cooling to room temperature, the solvent was removed in vacuo and the resulting residue was purified via flash silica gel chromatography (Analogix IF-280, SF25-115 g column, gradient 90:10-80:20 Heptane:EtOAc) to yield (E)-methyl 2-(cyclohexyloxy)-8-(4-methylthiazol-5-yl)oct-7-enoate. MS (ES+) 354 (M+1).

後処理

  1. customwas used in the next step without further purification
  2. customwas flushed with argon
  3. temperatureAfter cooling to room temperature
  4. customthe solvent was removed in vacuo
  5. customthe resulting residue was purified via flash silica gel chromatography (Analogix IF-280

出典と根拠

ORDレコード
ord-595cf626c9c040769cac23ef499480d1
出典データセット
uspto-grants-2013_07
特許番号
US08476302B2

反応ノート

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