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

HRID 129180

반응식

HRID 129180 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A solution of 6-cyano-2,2-dimethyl-2H-1-benzopyran (5.5 g, 29.7 mmoles, prepared according to Evans et al., J. Chem. Med., 1983, 26, p. 1582 and J. Med. Chem., 1986, 29, p. 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 a 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 which was used in the next step without further purification. 1H NMR (CDCl3) δ7.37 (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) δ157.95, 133.82, 131.34, 122.07, 119.53, 118.24, 102.66, 75,76, 32.13, 26.81, 22.06.

후처리

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

출처 및 근거

ORD 기록
ord-d0cb321d5f034a65a65d21633510b1ee
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466817

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