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

HRID 1427887
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HRID 1427887 반응식
[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
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 14798
Sodium Hydroxide
용매

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온도
0 °C

실험 절차

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);

후처리

  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

출처 및 근거

ORD 기록
ord-b17c9a45da384c52920f09d5c424c598
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08933236B2

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