Benzyl formate → 9-Formyl-2,7-fluorenedicarboxylic acid dibenzyl ester

HRID 1530165

反応式

HRID 1530165 の反応式
[CH2:1]([O:8][C:9]([C:11]1[CH:23]=[CH:22][C:21]2[C:20]3[C:15](=[CH:16][C:17]([C:24]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:25])=[CH:18][CH:19]=3)[CH2:14][C:13]=2[CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:34](OCC1C=CC=CC=1)=[O:35].CC(C)([O-])C.[K+]>C1COCC1>[CH2:27]([O:26][C:24]([C:17]1[CH:18]=[CH:19][C:20]2[C:21]3[C:13](=[CH:12][C:11]([C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])=[CH:23][CH:22]=3)[CH:14]([CH:34]=[O:35])[C:15]=2[CH:16]=1)=[O:25])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

参加物

5

反応物 3

HCID 7708Benzyl formateHCID 23665647Potassium tert-butoxideHCID 66910038Dibenzyl 9H-fluorene-2,7-dicarboxylate

生成物 1

HCID 866097799-Formyl-2,7-fluorenedicarboxylic acid dibenzyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

In a dry argon-purged flask, 2,7-fluorenedicarboxylic acid dibenzyl ester (3.0 g, 0.0065 mol) was dissolved in anh. THF (60 mL) at room temperature. Benzyl formate (4.2 mL, 0.035 mol, stored over anhydrous K2CO3) was added followed by addition of potassium tert-butoxide 95% (2.7 g, 0.023 mol). The reaction was stirred for three hours then the reaction was quenched with the addition of water and acidified with HCl to pH 2. The organic solvent was partially evaporated at reduced pressure. The product was twice extracted with ethyl acetate (600 mL then 200 mL). The combined organic layers were washed three times with brine, dried over sodium sulfate, filtered and evaporated to dryness. The crude product was washed with hexanes and methanol (1.9 g, 60%). 1H-NMR (d6-DMSO): δ (ppm) 11.9 (s, ˜1H, formyl); 8.8 (s, 1H, Ar); 8.5 (s, 1H, Ar); 8.4 (s, 1H, Ar); 8.2 (m, 2H, Ar); 7.9 (m, 2H, Ar); 7.5-7.4 (m, 10H, Bz); 5.4 (s, 4H, Ar).

後処理

  1. customIn a dry argon-purged flask
  2. customthe reaction was quenched with the addition of water
  3. customThe organic solvent was partially evaporated at reduced pressure
  4. extractionThe product was twice extracted with ethyl acetate (600 mL
  5. washThe combined organic layers were washed three times with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. washThe crude product was washed with hexanes and methanol (1.9 g, 60%)

出典と根拠

ORDレコード
ord-a4e984f6276243008d00e251a26118c8
出典データセット
uspto-grants-2015_07
特許番号
US09090740B2

関連ノート

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