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

HRID 717651

반응식

HRID 717651 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f19002aa3ef34a968b27faf7a99a7071
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193716B2

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