Dimethylformamide → 2-(4-(2-(6-Methoxy-2,3-dihydrobenzofuran-2-yl)ethyl)phenoxy)ethanol

HRID 717651ノート

反応式

HRID 717651 の反応式
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[O:14][C:15]3[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:16]=3[CH:17]=2)=[CH:7][CH:6]=1)(=O)[CH3:2].C([O-])([O-])=[O:25].[K+].[K+].CN(C=O)C>>[CH3:23][O:22][C:20]1[CH:19]=[CH:18][C:16]2[CH2:17][CH:13]([CH2:12][CH2:11][C:8]3[CH:9]=[CH:10][C:5]([O:4][CH2:1][CH2:2][OH:25])=[CH:6][CH:7]=3)[O:14][C:15]=2[CH:21]=1

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 666148704-((6-Methoxybenzofuran-2-yl)ethynyl)phenyl acetate

生成物 1

HCID 461995202-(4-(2-(6-Methoxy-2,3-dihydrobenzofuran-2-yl)ethyl)phenoxy)ethanol収率 117.2%

実験手順

To a stirred solution of the product of Step A (0.05 g, 0.19 mmol) and K2CO3 (0.05 g, 0.36 mmol) in anhydrous DMF (5 ml) ethyl-bromo acetate (0.025 ml, 0.22 mmol) was added at room temperature. The mixture was stirred for 2 h and quenched with saturated NH4Cl solution, extracted in EtOAc (100 ml) and washed with H2O. The organic layer was separated and dried over MgSO4 and filtered. The filtrate was evaporated to dryness to give the title compound (0.07 g; 100%), as pale oil. 1H-NMR (CDCl3) 7.10 (d, 2H, J=8.39 Hz); 6.97 (d, 1H, J=8.46 Hz); 6.80 (t, 2H, J=8.36 Hz); 6.35-6.33 (m, 2H); 4.75-4.71 (m, 1H); 4.56 (s, 2H); 4.22 (q, 2H, J=14.36, 7.17 Hz); 3.72 (s, 3H, OMe); 3.2-3.13 (m, 1H); 2.79-2.69 (m, 3H); 2.0-1.87 (m, 2H); 1.26 (t, 3H, J=7.12 Hz).

後処理

  1. customquenched with saturated NH4Cl solution
  2. extractionextracted in EtOAc (100 ml)
  3. washwashed with H2O
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

出典と根拠

ORDレコード
ord-f19002aa3ef34a968b27faf7a99a7071
出典データセット
uspto-grants-2015_11
特許番号
US09193716B2

反応ノート

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