Sodium ethoxide → 4-(benzofuran-2-ylmethoxy)benzyl 4-methyl-2-oxo-2H-chromen-7-ylcarbamate

HRID 2061383노트

반응식

HRID 2061383 반응식
[O-]CC.[Na+].[O:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]=[C:6]1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][OH:23])=[CH:18][CH:17]=1.[N:24]([C:27]1[CH:36]=[C:35]2[C:30]([C:31]([CH3:38])=[CH:32][C:33](=[O:37])[O:34]2)=[CH:29][CH:28]=1)=[C:25]=[O:26]>CN(C=O)C>[CH3:38][C:31]1[C:30]2[C:35](=[CH:36][C:27]([NH:24][C:25](=[O:26])[O:23][CH2:22][C:19]3[CH:20]=[CH:21][C:16]([O:15][CH2:14][C:6]4[O:5][C:9]5[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=5[CH:7]=4)=[CH:17][CH:18]=3)=[CH:28][CH:29]=2)[O:34][C:33](=[O:37])[CH:32]=1

참가 물질

5

반응물 3

HCID 2723922Sodium ethoxideHCID 583781007-isocyanato-4-methyl-2H-chromen-2-oneHCID 66601277(4-(Benzofuran-2-ylmethoxy)phenyl)methanol

생성물 1

HCID 596031424-(benzofuran-2-ylmethoxy)benzyl 4-methyl-2-oxo-2H-chromen-7-ylcarbamate수율 8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Sodium ethoxide (40 mg, 0.59 mmol) was added to DMF at 0° C., and the suspension was stirred for 10 min. (4-(benzofuran-2-ylmethoxy)phenyl)methanol (150 mg, 0.59 mmol), was added and resulting mixture was stirred at this temperature for 0.5 h, then allowed to reach room temperature. To this mixture 76 (130 mg, 0.65 mmol) was added portionwise. Resulting mixture was stirred at room temperature for 2 h. DMF was evaporated off in-vacuo. The crude residue was purified by flash chromatography, eluting with hexane: EtOAc (2:1) to give the target compound (20 mg, 8%) as a white solid. m/z=456.10 (M+H). H1 NMR (500 MHz, DMSO-d6): δ=10.22 (1H, bs, NH), 7.69-7.64 (2H, m, ArH), 7.58 (1H, d, J=8.15 Hz, ArH), 7.55 (1H, s, ArH), 7.42 (2H, d, J=8.00 Hz, ArH), 7.33 (1H, t, J=7.70 Hz, ArH), 7.26 (1H, t, J=7.5 Hz, ArH), 7.11 (2H, d, J=8.28 Hz, ArH), 7.06 (1H, s, ArH), 6.23 (1H, s, ArH), 5.29 (2H, s, CH2), 5.12 (2H, s, CH2), 2.37 (3H, s, CH3).

후처리

  1. additionwas added
  2. customresulting mixture
  3. customto reach room temperature
  4. customResulting mixture
  5. stirringwas stirred at room temperature for 2 h
  6. customDMF was evaporated off in-vacuo
  7. customThe crude residue was purified by flash chromatography
  8. washeluting with hexane: EtOAc (2:1)

출처 및 근거

ORD 기록
ord-75352e42a12b4ee7a75bd001c471d63a
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283340B2

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