1-[4-Acetyl-1-(2,4-dimethoxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone → 1-[4-acetyl-1-(2-hydroxy-4-methoxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone

HRID 2375403Notes

Reaction equation

[C:1]([C:4]1[C:5]([C:21](=[O:23])[CH3:22])=[C:6]([CH3:20])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18]C)[C:8]=1[CH3:9])(=[O:3])[CH3:2].C([S-])C.[Na+]>CN(C=O)C>[C:1]([C:4]1[C:5]([C:21](=[O:23])[CH3:22])=[C:6]([CH3:20])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[OH:18])[C:8]=1[CH3:9])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

To a stirring solution of 1-[4-acetyl-1-(2,4-dimethoxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone prepared as in Example 70 (1580 mg, 0.5 mmol) in 2.0 mL of dry DMF at rt was added sodium ethanethiolate (80%, Aldrich; 210 mg, 2.0 mmol). After 20 min at rt, it was heated to 120° C. and stirred for an additional 2 h before it was quenched with 1N HCl (5 mL). It was extracted with EtOAc (2×10 mL), and the combined organic extracts were washed with dried with MgSO4, filtered, and concentrated in vacuo to afford the crude product as a yellow oil. This crude material was purified by automated chromatography on silica gel (using an 20-50% EtOAc/hexanes gradient) to give the major product 1-[4-acetyl-1-(2-hydroxy-4-methoxy-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone as pale yellow oil: MS (ESI) 302 (M+H)+.

Workup

customat rt
customwas quenched with 1N HCl (5 mL)
extractionIt was extracted with EtOAc (2×10 mL)
washthe combined organic extracts were washed
dry with materialwith dried with MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto afford the crude product as a yellow oil
customThis crude material was purified by automated chromatography on silica gel (

Sources & evidence

ORD record: ord-6bd1ed56a897406296fe7c6adc7046e5
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465730B2

Reaction notes

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