Ammonia → HCID 68863993、化合物

HRID 1986615ノート

反応式

HRID 1986615 の反応式
[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

参加物

7

反応物 3

HCID 222AmmoniaHCID 24083Sulfuric acid magnesium salt (1:1)HCID 57722497HCID 57722497、化合物

生成物 1

HCID 68863993HCID 68863993、化合物収率 100%

試薬・触媒・溶媒 3

HCID 14801Manganese dioxide触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-843e29e1ac88451182f4212397eec8f0
出典データセット
uspto-grants-2009_06
特許番号
US07550467B2

反応ノート

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