Acetic Acid → HCID 135487639、化合物

HRID 1934504ノート

反応式

HRID 1934504 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH2:9][CH:10]([C:24]1[CH:29]=[CH:28][C:27]2[O:30][CH2:31][O:32][C:26]=2[CH:25]=1)[CH2:11][C:12]([C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=1)=O.CC(O)=O.C[N:39](C)C=O>>[O:30]1[C:27]2[CH:28]=[CH:29][C:24]([C:10]3[CH:11]=[C:12]([C:14]4[CH:23]=[CH:22][C:21]5[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=5)[CH:15]=4)[N:39]=[C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[OH:1])[CH:9]=3)=[CH:25][C:26]=2[O:32][CH2:31]1

参加物

4

反応物 3

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 18679600HCID 18679600、化合物

生成物 1

HCID 135487639HCID 135487639、化合物

反応条件

温度
100 °C

実験手順

A mixture of 1-(2-hydroxyphenyl)-3-(3,4-methylenedioxyphenyl)-5-(naphthalen-2-yl)-1,5-pentanedione on Wang resin (2.7 g, 1.68 mmol), NH4OAc (1.0 g), and AcOH (1.5 mL) in dimethylformamide (40 mL) was heated at 100° C. for 18 h. The resin was filtered, and washed with dimethylformamide (×2) and alternating MeOH and CH2Cl2 (×5), and dried under high vacuum overnight. The dried resin was treated with 50% TFA/CH2Cl2 (15 mL) for 1 h. After filtration of the reaction mixture, the filtrate was concentrated to dryness. The residue was repeatedly dissolved in CH2Cl2 (10 mL) and concentrated to remove traces of TFA. Purification by flash chromatography gave 2-(4benzo[1,3]dioxol-5-yl-6-naphthalen-2-yl-pyridin-2-yl)-phenol; mp 195-196° C.; 1H NMR (DMSO-d6) d 6.17 (s, 2H), 6.99 (m, 2H), 7.17 (d, J=8.2 Hz, 1H), 7.37 (m, 1H), 7.63 (m, 2H), 7.71 (dd, J=8.2, 1.9 Hz, 1H), 7.83 (d, J=1.8 Hz, 1H), 8.03 (m, 1H), 8.12 (m, 2H), 8.24 (dd, J=8.6, 1.8 Hz, 1H), 8.35 (m, 2H), 8.42 (d, J=1.1 Hz, 1H), 8.74 (s, 1H), 14.55 (s, 1H); IR (KBr) 1605 cm−1; MS [M+H]+ m/z=418. Anal. calcd for C28H19NO3: C, 80.56; H, 4.59; N, 3.36; Found: C, 80.13; H, 4.49; N, 3.18.

後処理

  1. filtrationThe resin was filtered
  2. washwashed with dimethylformamide (×2)
  3. customdried under high vacuum overnight
  4. additionThe dried resin was treated with 50% TFA/CH2Cl2 (15 mL) for 1 h
  5. filtrationAfter filtration of the reaction mixture
  6. concentrationthe filtrate was concentrated to dryness
  7. dissolutionThe residue was repeatedly dissolved in CH2Cl2 (10 mL)
  8. concentrationconcentrated
  9. customto remove traces of TFA
  10. customPurification by flash chromatography

出典と根拠

ORDレコード
ord-2561662611a34e869f411207eec7e0f0
出典データセット
uspto-grants-2002_05
特許番号
US06384057B1

反応ノート

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