Hydrochloric Acid → 1-(2-Chlorobenzofuran-5-yl)propan-1-one

HRID 626252Notes

Reaction equation

HRID 626252 reaction equation
[Cl:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]3([CH2:16][CH3:17])OCC[O:12]3)=[CH:7][C:5]=2[CH:6]=1.Cl>CO>[Cl:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11](=[O:12])[CH2:16][CH3:17])=[CH:7][C:5]=2[CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 896572452-Chloro-5-(2-ethyl-1,3-dioxolan-2-yl)benzofuran

Product 1

HCID 896729131-(2-Chlorobenzofuran-5-yl)propan-1-oneYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-chloro-5-(2-ethyl-1,3-dioxolan-2-yl)benzofuran (250 mg, 1.0 eq) in 15 mL MeOH was added 3 mL 3N HCl (aq) at rt. The reaction was stirred for 30 min at rt, quenched with sat NaHCO3 (aq), and extracted with EtOAc. The extract was washed with brine, dried, concentrated, and purified by column chromatography to give the desired product (140 mg, 68%). 1H NMR (400 MHz, CDCl3) δ 8.15 (d, J=1.6 Hz, 1H), 7.95 (dd, J=8.4 Hz, 1.6 Hz, 1H), 7.48 (d, J=8.8 Hz, 1H), 6.68 (s, 1H), 3.06 (q, J=6.8 Hz, 2H), 1.25 (t, J=6.8 Hz, 3H).

Workup

  1. customquenched with sat NaHCO3 (aq)
  2. extractionextracted with EtOAc
  3. washThe extract was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-7e77164896204c79bb3bccb4fd870967
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

Loading…