6-Methoxy-5-nitro-1,2,3,4-tetrahydronaphthalen-1-one → HCID 22244785、化合物

HRID 891175

反応式

HRID 891175 の反応式
[CH3:1][O:2][C:3]1[C:4]([N+:14]([O-:16])=[O:15])=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([Li])=[C:21]([O:26][CH3:27])[C:20]=1[O:28][CH3:29]>>[OH:13][C:9]1([C:23]2[CH:22]=[C:21]([O:26][CH3:27])[C:20]([O:28][CH3:29])=[C:19]([O:18][CH3:17])[CH:24]=2)[C:10]2[C:5](=[C:4]([N+:14]([O-:16])=[O:15])[C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH2:6][CH2:7][CH2:8]1

参加物

3

反応物 2

HCID 130673376-Methoxy-5-nitro-1,2,3,4-tetrahydronaphthalen-1-oneHCID 178506740HCID 178506740、化合物

生成物 1

HCID 22244785HCID 22244785、化合物収率 55%

実験手順

6-Methoxy-5-nitro-1-tetralone (21) (2.65 g, 12.0 mol) was added at −20° C. to the trimethoxyphenyllithium and stirring was continued for 2 h (−20° C. -RT). The mixture was partitioned between CH2Cl2 and water, the organic layer was dried over anhydrous sodium sulfate, and, after filtration, the organic layer was concentrated in vacuo, to afford 1-Hydroxy-6-methoxy-5-nitro-1-(3′,4′,5′-trimethoxyphenyl)tetralin (30) as a crude yellow oil. (GC-MS shows the yield is about 55%). This compound, without purification, was added to a refluxing mixture of acetic acid (10 mL) and water (80 mL), and iron (0.5 g) was added. After heating at reflux for 1 h, the mixture was partitioned between CH2Cl2 (3×100 mL) and water (100 mL). The organic layer was washed with NaHCO3 (sat.) and water (100 mL each), dried over anhydrous sodium sulfate, and, after filtration, the organic layer was concentrated in vacuo to provide a yellow oil. Purification by column chromatography afforded 5-Amino-6-methoxy-1-(3′,4′,5′-trimethoxyphenyl)-3,4-dihydronaphthalene (31):

後処理

  1. custom(−20° C. -RT)
  2. customThe mixture was partitioned between CH2Cl2 and water
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. filtrationafter filtration
  5. concentrationthe organic layer was concentrated in vacuo

出典と根拠

ORDレコード
ord-6bbfcb19611c44d39bcd2d06c9d4cf13
出典データセット
uspto-grants-2006_02
特許番号
US07001926B2

関連ノート

読み込み中…