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Trifluoroacetic acid → 4-(Adamantan-1-ylmethoxy)-3-cyclobutylbenzonitrile

HRID 1427887
ノート
印刷プレビュー

反応式

HRID 1427887 の反応式
[C:1]12([CH2:11][O:12][C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][C:14]=3[C:21]3(O)[CH2:24][CH2:23][CH2:22]3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl.[OH-].[Na+]>[C:1]12([CH2:11][O:12][C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][C:14]=3[CH:21]3[CH2:24][CH2:23][CH2:22]3)[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 867029124-(Adamantan-1-ylmethoxy)-3-(1-hydroxycyclobutyl)benzonitrile

生成物 1

HCID 867029134-(Adamantan-1-ylmethoxy)-3-cyclobutylbenzonitrile

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 14798
Sodium Hydroxide
溶媒

反応条件

温度
0 °C

実験手順

To a cooled (0° C.) stirred solution of 4-(adamantan-1-ylmethoxy)-3-(1-hydroxycyclobutyl)-benzonitrile (1.00 g, 2.96 mmol) in methylene chloride (30 mL) was added triethylsilane (2.4 mL, 14.80 mmol) followed by trifluoroacetic acid (2.3 mL, 29.60 mmol). The reaction mixture was stirred at 0° C. for 1.5 h and diluted with 1M aqueous sodium hydroxide solution (30 mL). The mixture was extracted with methylene chloride (3×50 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a 5% to 10% gradient of ethyl acetate in hexanes to afford 4-(adamantan-1-ylmethoxy)-3-cyclobutylbenzonitrile as colorless solid in quantitative yield (0.95 g): MS (ES+) m/z 322.2 (M+1);

後処理

  1. extractionThe mixture was extracted with methylene chloride (3×50 mL)
  2. washThe combined organic layers were washed with brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. washeluting with a 5% to 10% gradient of ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-b17c9a45da384c52920f09d5c424c598
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08933236B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート