6,13-Pentacenequinone → HCID 178521537、化合物

HRID 1895565

反応式

HRID 1895565 の反応式
[CH:1]1[C:22]2[C:5](=[CH:6][C:7]3[C:8](=[O:24])[C:9]4[C:18]([C:19](=[O:23])[C:20]=3[CH:21]=2)=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=4)[CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[OH:23][C@H:19]1[C:18]2[C:9](=[CH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[C@H:8]([OH:24])[C:7]2[CH:6]=[C:5]3[C:22]([CH:1]=[CH:2][CH:3]=[CH:4]3)=[CH:21][C:20]1=2

参加物

4

反応物 2

HCID 764156,13-PentacenequinoneHCID 4311764Sodium borohydride

生成物 1

HCID 178521537HCID 178521537、化合物収率 91%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

To a suspension of 6,13-pentacenequinone (1.0 g, 3.24 mmol) in dry MeOH (40 mL) at 0° C. under an argon atmosphere was slowly added NaBH4 (1.22 g, 32.46 mmol). The reaction mixture was stirred at 0° C. for 0.5 h and at RT for 1 h, and then quenched with H2O at 0° C. The resulting mixture was filtered and washed with H2O. The resulting solid was taken up in CHCl3, then filtered and washed with CHCl3, and dried in vacuo to give product as an off-white solid (0.92 g, 91%): mp 235° C. 1H NMR (500 MHz, DMSO-d6): δ 8.12 (s, 4H), 7.95 (m, 4H), 7.48 (m, 4H), 6.63 (s, 2H), 5.81 (s, 2H). 13C NMR (125.68 MHz, DMSO-d6): δ 138.19, 131.67, 127.47, 125.44, 120.91, 66.98. LDI-MS m/z: 312 [M+], 296 [M+-OH], 280 [M+-2(OH)].

後処理

  1. customquenched with H2O at 0° C
  2. filtrationThe resulting mixture was filtered
  3. washwashed with H2O
  4. filtrationfiltered
  5. washwashed with CHCl3
  6. customdried in vacuo

出典と根拠

ORDレコード
ord-be057a0002e1450a959314afc1d4a9d8
出典データセット
uspto-grants-2013_08
特許番号
US08513466B2

関連ノート

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