4-Nitrophenyl chloroformate → HCID 15382527, compound

HRID 2061372Notes

Reaction equation

HRID 2061372 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][OH:11].Cl[C:13]([O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)=[O:14]>C1COCC1>[C:13](=[O:14])([O:15][C:16]1[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=1)[O:11][CH2:10][C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 27762631-Benzofuran-2-Ylmethanol

Product 1

HCID 15382527HCID 15382527, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzofuran-2-ylmethanol 59 (300 mg, 2.03 mmol) in THF (5 mL) was cooled to 0° C. TEA (280 μL, 2.03 mmol) was added dropwise followed by the portionwise addition of p-nitrophenyl chloroformate (282 mg, 3.05 mmol). The resulting solution was stirred at room temperature for 2 h. Solvent was evaporated off in vacuo and the crude residue was purified by flash chromatography, eluting with hexane:EtOAc (3:1) to give 60 (350 mg, 54%) as a white solid. H1 NMR (500 MHz, CDCl3): δ=8.31 (2H, m, ArH), 7.62 (1H, d, J=7.70 Hz, ArH), 7.54 (1H, d, J=7.70 Hz, ArH), 7.43-7.27 (3H, m, ArH), 7.29 (1H, t, J=7.72 Hz, ArH), 6.93 (1H, s, ArH), 5.43 (2H, s, CH2). 13C NMR CDEPT 135, (500 MHz, CDCl3): δ=125.47, 125.37, 123.23, 121.80, 121.66, 111.60, 108.53, 62.95.

Workup

  1. customSolvent was evaporated off in vacuo
  2. customthe crude residue was purified by flash chromatography
  3. washeluting with hexane:EtOAc (3:1)

Sources & evidence

ORD record
ord-d297c3f567b34a8299ae610a96a7d095
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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