Hexane → 4-(3-Furyl)-7-methylcoumarin

HRID 260440Notes

Reaction equation

HRID 260440 reaction equation
Br[C:2]1[CH:6]=[CH:5][O:4][CH:3]=1.[Li]CCCC.CCCCCC.B(OC)(OC)OC.[CH3:25][C:26]1[CH:35]=[C:34]2[C:29]([C:30](OS(C(F)(F)F)(=O)=O)=[CH:31][C:32](=[O:36])[O:33]2)=[CH:28][CH:27]=1>CCOCC.C1COCC1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[O:4]1[CH:5]=[CH:6][C:2]([C:30]2[C:29]3[C:34](=[CH:35][C:26]([CH3:25])=[CH:27][CH:28]=3)[O:33][C:32](=[O:36])[CH:31]=2)=[CH:3]1

Participants

11

Reactant 5

HCID 8058HexaneHCID 8470Trimethyl borateHCID 891643-BromofuranHCID 233702387-Methyl-2-oxo-2H-chromen-4-YL trifluoromethanesulfonateHCID 178418339Butyllithium

Product 1

HCID 233701904-(3-Furyl)-7-methylcoumarin

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 3-bromofuran (1.9 g, 12.7 mmol) in dry Et2O (30 mL) at -70° C. was added BuLi in hexane (1.9M, 6.7 mL, 12.7 mmol) and the resulting mixture was stirred for 20 min. Trimethyl borate (Aldrich) (1.4 mL, 12.7 mmol) was added dropwise and the mixture stirred for 20 min. A solution of the triflate from Step 4 in THF: H2O (24 mL: 6 mL) containing (Ph3P)4Pd (1.1 g, 0.97 mmol) was added and the reaction was heated to reflux for 16 h. The reaction mixture was cooled to r.t. and EtOAc was added and the organic phase washed with H2O (3×), brine, dried over MgSO4 and evaporated to give a white solid. A swish in EtOAc gave after filtration 1.8 g (82%) of the title compound.

Workup

  1. stirringthe mixture stirred for 20 min
  2. additionwas added
  3. temperaturethe reaction was heated
  4. temperatureto reflux for 16 h
  5. washthe organic phase washed with H2O (3×), brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customto give a white solid
  9. filtrationafter filtration 1.8 g (82%) of the title compound

Sources & evidence

ORD record
ord-89d4e7c4f1b54a3aabd6dae74ff93cae
Source dataset
uspto-grants-1996_06
Patent number
US05527827

Reaction notes

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