Diethyl Ether → 2-(3-(3-(Benzyloxy)phenyl)propyl)isoindoline-1,3-dione

HRID 74354

反応式

HRID 74354 の反応式
CCOCC.[OH:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][CH2:15][N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])[CH:10]=[CH:11][CH:12]=1.[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1>[CH2:27]([O:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][CH2:15][N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])[CH:10]=[CH:11][CH:12]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 580275422-[3-(3-Hydroxyphenyl)propyl]isoindole-1,3-dione

生成物 1

HCID 673166422-(3-(3-(Benzyloxy)phenyl)propyl)isoindoline-1,3-dione

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
70 °C

実験手順

Instead of a Mitsunobu reaction, the ether was formed by alkylation as described. A suspension of phenol 58 (1 g, 3.5 mmol), benzyl bromide (0.3 mL, 3.5 mmol), cesium carbonate (1.158 g, 3.5 mmol) in NMP (3.5 mL) was heated at 70° C. for 24 h. The reaction mixture was quenched by the addition of water, extracted with DCM, washed with water, and dried over anhy. Na2SO4. Filtration and concentration under reduced pressure gave the crude product, which was purified by flash chromatography (hexane-ethyl acetate (0-30%) gradients) to give 2-(3-(3-(benzyloxy)phenyl)propyl)isoindoline-1,3-dione as a white solid. Yield (0.708 g, 55%): 1H NMR (400 MHz, DMSO-d6) δ 7.81-7.84 (m, 2H), 7.69-7.72 (m, 2H), 7.30-7.44 (m, 5H), 7.13-7.18 (m, 1H), 6.83-6.85 (m, 1H), 6.80 (d, J=7.6 Hz, 1H), 6.74 (dd, J=7.8, 2.0, 1H), 5.03 (s, 2H), 3.74 (t, J=7.2 Hz, 2H), 2.67 (t, J=7.6 Hz, 2H), 2.0-2.08 (m, 2H).

後処理

  1. customInstead of a Mitsunobu reaction
  2. customThe reaction mixture was quenched by the addition of water
  3. extractionextracted with DCM
  4. washwashed with water
  5. customdried over anhy
  6. filtrationFiltration and concentration under reduced pressure
  7. customgave the crude product, which
  8. customwas purified by flash chromatography (hexane-ethyl acetate (0-30%) gradients)

出典と根拠

ORDレコード
ord-5b72be5d12984ac3b3ad52285c35b1d9
出典データセット
uspto-grants-2014_09
特許番号
US08829244B2

関連ノート

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