4-Nitrophenyl chloroformate → HCID 66601182, compound

HRID 2061373Notes

Reaction equation

HRID 2061373 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:14][CH3:15])[C:6]2[O:10][C:9]([CH2:11][OH:12])=[CH:8][C:7]=2[CH:13]=1.Cl[C:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=[O:18]>C1COCC1>[C:17](=[O:18])([O:19][C:20]1[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=1)[O:12][CH2:11][C:9]1[O:10][C:6]2[C:5]([O:14][CH3:15])=[CH:4][C:3]([O:2][CH3:1])=[CH:13][C:7]=2[CH:8]=1

Participants

4

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 59603165HCID 59603165, compound

Product 1

HCID 66601182HCID 66601182, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (5,7-dimethoxybenzofuran-2-yl)methanol 6 (100 mg, 0.48 mmol) in THF (3 mL) was cooled to 0° C. TEA (69 uL, 0.48 mmol) was added dropwise followed by the portionwise addition of p-nitrophenyl chloroformate (100 mg, 0.72 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 61 (120 mg, 67%) as a white solid. H1 NMR (500 MHz, CDCl3): δ=8.29 (2H, d, J=9.0 Hz, ArH), 7.40 (2H, d, J=9.0 Hz, ArH), 6.82 (1H, s, ArH), 6.63 (1H, s, ArH), 6.52 (1H, s, ArH), 5.39 (2H, s, CH2), 4.00 (3H, s, OCH3), 3.85 (3H, s, OCH3).

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-d64251181fe245b0a927dfa2e3f39100
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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