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

HRID 2061383Notes

Reaction equation

HRID 2061383 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-75352e42a12b4ee7a75bd001c471d63a
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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