Cesium carbonate → 2-(2-(3-(1-Hydroxy-cyclooctylmethoxy)-phenoxy)-ethyl)-isoindole-1,3-dione

HRID 74396ノート

反応式

HRID 74396 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[O:5][CH2:6][CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].[O:22]1[C:24]2([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:23]1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[OH:22][C:24]1([CH2:23][O:1][C:2]2[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=2)[O:5][CH2:6][CH2:7][N:8]2[C:9](=[O:18])[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]2=[O:17])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 132407571-Oxaspiro[2.7]decaneHCID 580275342-[2-(3-Hydroxy-phenoxy)-ethyl]-isoindole-1,3-dione

生成物 1

HCID 673174532-(2-(3-(1-Hydroxy-cyclooctylmethoxy)-phenoxy)-ethyl)-isoindole-1,3-dione

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
120 °C

実験手順

The suspension of phenol 24 (1.0 g, 3.5 mmol), 1-oxa-spiro[2.7]decane (0.5 g, 3.2 mmol) and Cs2CO3 (1.14 g, 3.5 mmol) in DMSO (4 mL) was heated at 120° C. for 16 h. After completion of reaction, the mixture was quenched by the addition of 1N HCl and extracted with DCM. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification by flash chromatography (0 to 10% 7N NH3/methanol—CH2Cl2) afforded 2-(2-(3-(1-hydroxy-cyclooctylmethoxy)-phenoxy)-ethyl)-isoindole-1,3-dione as yellow oil. Yield (0.53 g, 35%): 1H NMR (400 MHz, CDCl3) δ 7.92-7.98 (m, 1H), 7.40-7.51 (m, 3H), 7.08-7.14 (m, 1H), 6.45-6.54 (m, 3H), 4.03 (s, 2H), 3.68-3.76 (m, 2H), 1.35-1.92 (m, 16H).

後処理

  1. customAfter completion of reaction
  2. customthe mixture was quenched by the addition of 1N HCl
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography (0 to 10% 7N NH3/methanol—CH2Cl2)

出典と根拠

ORDレコード
ord-6991a04058864e32abf09d2288600b3a
出典データセット
uspto-grants-2014_09
特許番号
US08829244B2

反応ノート

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