6,13-Pentacenequinone → HCID 178521537, 화합물

HRID 1895565

반응식

HRID 1895565 반응식
[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

참가 물질

4

반응물 2

HCID 764156,13-PentacenequinoneHCID 4311764Sodium borohydride

생성물 1

HCID 178521537HCID 178521537, 화합물수율 91%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

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)].

후처리

  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

출처 및 근거

ORD 기록
ord-be057a0002e1450a959314afc1d4a9d8
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513466B2

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