Ammonia → HCID 68863993, 화합물

HRID 1986615노트

반응식

HRID 1986615 반응식
[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=O)=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]21[O:16][CH2:15][CH2:14][O:13]2.[NH3:17].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.C(Cl)Cl.O=[Mn]=O>[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:17])=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]21[O:16][CH2:15][CH2:14][O:13]2

참가 물질

7

반응물 3

HCID 222AmmoniaHCID 24083Sulfuric acid magnesium salt (1:1)HCID 57722497HCID 57722497, 화합물

생성물 1

HCID 68863993HCID 68863993, 화합물수율 100%

시약·촉매·용매 3

HCID 14801Manganese dioxide촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

Following the literature procedure of Lai, G. et al. (Synleft, 2001, 230-231), a stirred solution of 3′,4′-dihydro-1′H-spiro[[1,3]dioxolane-2,2′-naphthalene]-6′-carbaldehyde (440 mg, 2.0 mmol) in THF (2 mL) was charged with NH3 (2M solution in isopropanol, 15 mL, 30 mmol, 15 eq) and anhydrous MgSO4 (3.64 g, 30 mmol, 15 eq). After 1 hour, MnO2 (Aldrich, 85%, 3.1 g, 30 mmol, 15 eq) was added in small portions and the resulting mixture was stirred at room temperature for 20 hours. The reaction mixture was diluted with CH2Cl2 (40 mL) and filtered through Celite. The filtrate was concentrated in vacuo to give 0.42 g (100%) of 3′,4′-dihydro-1′H-spiro[[1,3]dioxolane-2,2′-naphthalene]-6′-carbonitrile as a brown oil. 1H NMR (300 MHz, CDCl3): δ 7.42 (s, 1H), 7.40 (d, 1H, J=8.0 Hz), 7.12 (d, 1H, J=8.0 Hz), 4.03 (s, 4H), 3.02 (s, 2H), 3.00 (t, 2H, J=6.9 Hz), 1.96 (t, 2H, J=6.9 Hz). The material was sufficiently pure and it was used in the next step without further purification.

후처리

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-843e29e1ac88451182f4212397eec8f0
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550467B2

반응 노트

불러오는 중…