Acetone → DBF

HRID 2229100ノート

反応式

HRID 2229100 の反応式
[CH:1]1[CH:2]=[CH:3][C:4]([C:23]([OH:25])=[O:24])=[C:5]([C:7]2[C:17]3[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:16]=3[O:15][C:14]3[C:8]=2[CH:9]=[CH:10][C:11]([CH:13]=3)=[O:12])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:32](Cl)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[CH3:40][C:41]([CH3:43])=O>CN(C)C=O>[CH:36]1[CH:37]=[CH:38][C:33]([CH2:32][O:12][C:11]2[CH:10]=[CH:9][C:8]3[C:7]([C:5]4[C:4]([C:23]([O:25][CH2:40][C:41]5[CH:43]=[CH:5][CH:6]=[CH:1][CH:2]=5)=[O:24])=[CH:3][CH:2]=[CH:1][CH:6]=4)=[C:17]4[C:16]([O:15][C:14]=3[CH:13]=2)=[CH:21][C:20](=[O:22])[CH:19]=[CH:18]4)=[CH:34][CH:35]=1

参加物

6

反応物 4

HCID 180AcetoneHCID 33832-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acidHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

生成物 1

HCID 371436DBF

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Fluorescein (40 g, 120.5 mmol) was dissolved in dimethylformamide (DMF, 500 mL) in a 2 L flask fitted with a mechanical stirrer then potassium carbonate (72 g, 521.7 mmol) was added in as a single portion. The reaction was heated to 80° C. then benzyl chloride (42 mL, 363.5 mmol) was added dropwise. After 24 h at 80° C. the reaction was cooled down to room temperature. Acetone (400 mL) was added and the product was allowed to precipitate overnight. The solid orange product was filtered, washed with acetone and dried in a vacuum oven at 50° C. The O-benzylfluorescein benzyl ester was obtained as an orange solid (36.4 g, 59%): mp 192-193° C. (Lit. 193-194° C.); 1H NMR (DMSO-d6): 4.97 (dd, 2H, J=12.2 Hz, J=15.3 Hz), 5.28 (s, 2H), 6.13 (d, 1H, J=1.9 Hz), 6.36 (dd, 1H, J=9.9 Hz), 6.77 (d, 1H, J=9.9 Hz), 6.82 6.77 (d, 1H, J=9.0 Hz), 6.90-6.98 (m, 3H), 7.14-7.27 (m, 4H), 7.33-7.52 (m, 6H), 7.78 (dt, 1H, J=1.65 Hz, J=7.4 Hz), 8.23 (dd, 1H, J=1.35 Hz, J=7.7 Hz); 13C NMR (DMSO-d6): 67.4, 70.7, 101.9, 105.2, 114.7, 115.0, 117.3, 128.3, 128.5, 128.7, 128.8, 128.9, 129.4, 130.0, 130.2, 130.6, 130.8, 131.2, 131.4, 133.8, 134.1, 135.3, 136.6, 150.1, 153.9, 158.7, 163.3, 165.5, 184.4; IR (nujol) cm−1 1728, 1643, 1595, 1517, 1462, 1377, 1261, 1211, 1081, 855. C34H24O5: Calc.(C, 79.67; H, 4.72) Found (C, 79.74; H, 4.79).

後処理

  1. customfitted with a mechanical stirrer
  2. temperatureAfter 24 h at 80° C. the reaction was cooled down to room temperature
  3. customto precipitate overnight
  4. filtrationThe solid orange product was filtered
  5. washwashed with acetone
  6. customdried in a vacuum oven at 50° C

出典と根拠

ORDレコード
ord-b7614599a773446caf015d8577b37e98
出典データセット
uspto-grants-2002_07
特許番号
US06420131B1

反応ノート

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