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

HRID 445404노트

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HRID 445404 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-595cf626c9c040769cac23ef499480d1
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476302B2

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