2,2-dimethyl-2H-1-benzopyran-6-carbonitrile → 6-Cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

HRID 847173

反応式

HRID 847173 の反応式
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH:9]=[CH:8][C:7]=2[CH:14]=1)#[N:2]>C(O)C.[Pd]>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:12])([CH3:13])[CH2:9][CH2:8][C:7]=2[CH:14]=1)#[N:2]

参加物

4

反応物 1

HCID 27790742,2-dimethyl-2H-1-benzopyran-6-carbonitrile

生成物 1

HCID 109212656-Cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran収率 102.7%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A solution of 6-cyano-2,2-dimethyl-2H-1-benzopyran (5.5 g, 29.7 mmoles, prepared according to Evans et al., J. Med. Chem., 1983, 26, 1582 and J. Med. Chem. 1986, 29, 2194) in anhydrous ethanol (40 ml) was treated with palladium on carbon (0.35 g) and stirred under hydrogen gas for 2 hours. The catalyst was filtered through celite and the filter cake washed with ethyl acetate. The filtrate was concentrated under vacuum to obtain 5.71 g of a yellow oil. The crude product was dissolved in ethyl acetate (60 ml) and washed successively with 5% hydrogen chloride solution (60 ml), saturated sodium hydrogen carbonate solution (60 ml), saturated sodium chloride solution (60 ml) and dried over anhydrous magnesium sulfate. The solvent was recovered under vacuum to yield 5.14 g of the title A compound as a yellow solid (m.p. 30°-31° C.) which was used in the next step without further purification. 1H NMR (CDCl3) δ 7.37 (s, 1H), 7.34 (s, 1H), 6.80 (d, J=8.8 Hz, 1H), 2.78 (dd, 2H), 1.80 (dd, 2H), 1.35 (s, 6H). 13C NMR (CDCl3) δ 157.95, 133.82, 131.34, 122.07, 119.53, 118.24, 102.66, 75.76, 32.13. 26.81. 22.06.

後処理

  1. filtrationThe catalyst was filtered through celite
  2. washthe filter cake washed with ethyl acetate
  3. concentrationThe filtrate was concentrated under vacuum

出典と根拠

ORDレコード
ord-76acc03c0d58461986b111192297bdba
出典データセット
uspto-grants-1992_08
特許番号
US05140031

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