Sodium hydride → HCID 67367570, compound

HRID 1910900Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7].[H-].[Na+].Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][OH:23])=[CH:18][CH:17]=1)=[O:15].[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O>[OH:23][CH2:22][C:19]1[CH:20]=[CH:21][C:16]([C:14](=[O:15])[CH2:13][N:1]2[CH:5]=[CH:4][CH:3]=[C:2]2[C:6]([O:8][CH3:9])=[O:7])=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a chilled solution of methyl 2-pyrrolecarboxylate (500 mg, 4.0 mmol) in dry DMF (15 mL) was added sodium hydride (60% dispersion in mineral oil, 300 mg, 7.5 mmol) portion wise. The mixture was stirred at 0° C. for 1 hour and a solution of 2-bromo-1-[4-(hydroxymethyl)phenyl]ethanone (750 mg, 3.3 mmol) in DMF (5 mL) was added and the mixture was allowed to warm to room temperature and stirred for 1.5 hour. A saturated aqueous solution of NH4Cl (35 mL) was added followed by EtOAc (100 mL). The organic layer was then washed with brine (35 mL), dried (MgSO4), filtered and concentrated in vacuo to yield a oil. The material was purified by flash chromatography (Biotage SP4, 40 g cartridge, gradient 0-80% EtOAc in hexanes) to give methyl 1-{2-[4-(hydroxymethyl)phenyl]-2-oxoethyl}-1H-pyrrole-2-carboxylate as a white solid (150 mg, yield: 17%). ESI-MI m/z [M+H]+: 273.8.

Workup

temperatureto warm to room temperature
stirringstirred for 1.5 hour
washThe organic layer was then washed with brine (35 mL)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customto yield a oil
customThe material was purified by flash chromatography (Biotage SP4, 40 g cartridge, gradient 0-80% EtOAc in hexanes)

Sources & evidence

ORD record: ord-759df58ce5244c539b17df65f917bfd7
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604034B2

Reaction notes

Loading…