Boron trifluoride etherate → 2,2-Dimethyl-4-(4-methylphenyl)-4-(prop-2-en-1-yl)oxane

HRID 76219

反応式

HRID 76219 の反応式
[CH2:1]([Si](C)(C)C)[CH:2]=[CH2:3].[CH3:8][C:9]1([CH3:23])[CH2:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(O)[CH2:12][CH2:11][O:10]1.B(F)(F)F.O(CC)CC>C(Cl)Cl>[CH3:8][C:9]1([CH3:23])[CH2:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)([CH2:3][CH:2]=[CH2:1])[CH2:12][CH2:11][O:10]1

参加物

5

反応物 3

HCID 8000Boron trifluoride etherateHCID 69808AllyltrimethylsilaneHCID 641378172,2-Dimethyl-4-(4-methylphenyl)oxan-4-ol

生成物 1

HCID 683142852,2-Dimethyl-4-(4-methylphenyl)-4-(prop-2-en-1-yl)oxane

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Allyltrimethylsilane (4.34 ml, 27.2 mmol) was added to a solution of 2,2-dimethyl-4-(4-methylphenyl)oxan-4-ol (3.0 g, 13.6 mmol) in dry CH2Cl2 (100 ml) at 0° C., followed by BF3—OEt2 (3.42 ml, 27.2 mmol). The resulting mix was stirred at 0° C. for 1 h. The reaction was quenched with H2O (10 ml) and diluted with CH2Cl2 (10 ml), and washed with sat. NaHCO3 (20 ml), brine (20 ml), dried and concentrated. Purified by normal phase SiO2 chromatography (5 to 40% EtOAc/hexanes) to give 2,2-dimethyl-4-(4-methylphenyl)-4-(prop-2-en-1-yl)oxane as a colorless oil, which was used crude (2.49 g, 75%).

後処理

  1. additionThe resulting mix
  2. customThe reaction was quenched with H2O (10 ml)
  3. additiondiluted with CH2Cl2 (10 ml)
  4. washwashed with sat. NaHCO3 (20 ml), brine (20 ml)
  5. customdried
  6. concentrationconcentrated
  7. customPurified by normal phase SiO2 chromatography (5 to 40% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-4194aaae1920413e9a917b02d374f89a
出典データセット
uspto-grants-2014_09
特許番号
US08835488B2

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