[4-(2-Furyl)phenyl]methanol → 4-(furan-2-yl)benzyl 4-methyl-2-oxo-2H-chromen-7-ylcarbamate

HRID 2061378Notes

Reaction equation

HRID 2061378 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][CH:7]=1.[N:14]([C:17]1[CH:26]=[C:25]2[C:20]([C:21]([CH3:28])=[CH:22][C:23](=[O:27])[O:24]2)=[CH:19][CH:18]=1)=[C:15]=[O:16]>C1COCC1>[CH3:28][C:21]1[C:20]2[C:25](=[CH:26][C:17]([NH:14][C:15](=[O:16])[O:13][CH2:12][C:9]3[CH:10]=[CH:11][C:6]([C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)=[CH:7][CH:8]=3)=[CH:18][CH:19]=2)[O:24][C:23](=[O:27])[CH:22]=1

Participants

4

Reactant 2

HCID 7537506[4-(2-Furyl)phenyl]methanolHCID 583781007-isocyanato-4-methyl-2H-chromen-2-one

Product 1

HCID 596031594-(furan-2-yl)benzyl 4-methyl-2-oxo-2H-chromen-7-ylcarbamateYield 9.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4-(Furan-2-yl)phenyl)methanol (100 mg, 0.57 mmol) and 76 (139 mg, 0.69 mmol) were dissolved in THF (10 mL). The resulting mixture was stirred at room temperature for 15 min and then at 80° C. for 1 h. THF was evaporated off in vacuo. The residue was adsorbed on silica and purified by flash chromatography, eluting with CH2Cl2/EtOAc (1:1) to give the target compound (20 mg, 9%) as a white solid. m/z=376.11 (M+H), 751.22 (2M+H).

Workup

  1. waitat 80° C. for 1 h
  2. customTHF was evaporated off in vacuo
  3. custompurified by flash chromatography
  4. washeluting with CH2Cl2/EtOAc (1:1)

Sources & evidence

ORD record
ord-73ebde5eabfd4b04ab0a7288ffa45a99
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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