Boron trifluoride etherate → 5,6-Dimethoxy-3,4-dihydronaphthalene-1-carbonitrile

HRID 2199534ノート

反応式

HRID 2199534 の反応式
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=O.[Si]([C:20]#[N:21])(C)(C)C.B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]=[C:8]2[C:20]#[N:21]

参加物

5

反応物 3

HCID 8000Boron trifluoride etherateHCID 82115Trimethylsilyl cyanideHCID 82192465,6-dimethoxy-1-tetralone

生成物 1

HCID 135385495,6-Dimethoxy-3,4-dihydronaphthalene-1-carbonitrile収率 96%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Tetralone 7 (1.7 g, 8.25 mmol) was added as a slurry in freshly distilled toluene (25 mL) to a dried flask with magnetic stirring. TMSCN (1.42 mL, 10.7 mmol) was added dropwise. After stirring for 10 min, BF3.OEt2 (1.57 mL, 12.38 mmol) was added with a syringe. The reaction was stirred at room temperature for 3 h, until no starting material remained. The reaction was quenched by pouring over 30 mL ice water and stirring vigorously. To this aqueous mixture were added 20 mL of Et2O, and the layers were separated. The aqueous layer was extracted twice more with Et2O and once with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and evaporated under reduced pressure to afford a tan solid (1.7 g, 7.9 mmol, 96%) that was recrystallized from MeOH to yield fine, colorless needles; mp 138-140° C. (lit.36 mp 137-139° C.). 1H NMR: (300 MHz, CDCl3): δ 7.18 (d, 1H, J=8 Hz, ArH); 6.80 (d, 1H, J=8 Hz, ArH); 6.75 (t, 1H, J=4.6 Hz, ArCH2CH2CH); 3.88 (s, 3H, ArOCH3); 3.76 (s, 3H, ArOCH3); 2.87 (t, 2H, J=8 Hz, ArCH2); 2.44 (m, 2H, ArCH2CH2). EIMS (M+)=215.

後処理

  1. stirringThe reaction was stirred at room temperature for 3 h, until no starting material
  2. customThe reaction was quenched
  3. additionby pouring over 30 mL ice water
  4. stirringstirring vigorously
  5. additionTo this aqueous mixture were added 20 mL of Et2O
  6. customthe layers were separated
  7. extractionThe aqueous layer was extracted twice more with Et2O and once with EtOAc
  8. dry with materialThe combined organic layers were dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-ed83d81b65fc495baa3ad821c24cf8b7
出典データセット
uspto-grants-2016_06
特許番号
US09359303B2

反応ノート

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