Ethylparaben → 4-[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-cyclohexyloxy]-benzoic acid ethyl ester

HRID 555377ノート

反応式

HRID 555377 の反応式
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH2:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:38]([O:40][C:41](=[O:49])[C:42]1[CH:47]=[CH:46][C:45](O)=[CH:44][CH:43]=1)[CH3:39].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:38]([O:40][C:41](=[O:49])[C:42]1[CH:47]=[CH:46][C:45]([O:1][CH:2]2[CH2:3][CH2:4][CH:5]([N:8]3[C:9](=[O:18])[C:10]4[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:16]3=[O:17])[CH2:6][CH2:7]2)=[CH:44][CH:43]=1)[CH3:39]

参加物

6

反応物 4

HCID 8434EthylparabenHCID 11776TriphenylphosphineHCID 288726trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dioneHCID 5363146Diisopropyl azodicarboxylate

生成物 1

HCID 167566294-[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-cyclohexyloxy]-benzoic acid ethyl ester収率 42%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 2-(4-hydroxycyclohexyl)isoindole-1,3-dione (8.0 g, 32.6 mmol) in dry THF (100 mL) was added triphenyl phosphine (12.8 g, 48.8 mmol) and 4-hydroxy benzoic acid ethyl ester (5.44 g, 32.7 mmol). The reaction mixture was cooled to 0° C. and DIAD (9.6 g, 47.4 mmol) was added dropwise from an addition funnel over a period of 3 h. The reaction was gradually brought to room temperature and stirring continued for 3 h. The solvent was removed under vacuum and ether (100 mL) was added and cooled to 0° C. The solid formed was filtered and the clear filtrate concentrated and purified by column chromatography over neutral alumina (8% AcOEt in hexane) to give 5.13 g (42%) of 4-[4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-cyclohexyloxy]-benzoic acid ethyl ester.

後処理

  1. customwas gradually brought to room temperature
  2. customThe solvent was removed under vacuum and ether (100 mL)
  3. additionwas added
  4. temperaturecooled to 0° C
  5. customThe solid formed
  6. filtrationwas filtered
  7. concentrationthe clear filtrate concentrated
  8. custompurified by column chromatography over neutral alumina (8% AcOEt in hexane)

出典と根拠

ORDレコード
ord-08a2286d0f1248b2a2d202b1fc2db021
出典データセット
uspto-grants-2011_11
特許番号
US08053447B2

反応ノート

読み込み中…