Phenylacetone → Ethyl 4-(1-hydroxy-1-methyl-2-phenylethyl)-3-nitrobenzoate

HRID 1261565Notes

Reaction equation

II.[Mg].[CH2:4]([O:6][C:7](=[O:18])[C:8]1[CH:13]=[CH:12][C:11](I)=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1)[CH3:5].C1([Mg]Cl)C=CC=CC=1.[Li+].[Cl-].[C:29]1([CH2:35][C:36](=[O:38])[CH3:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[OH:38][C:36]([C:11]1[CH:12]=[CH:13][C:8]([C:7]([O:6][CH2:4][CH3:5])=[O:18])=[CH:9][C:10]=1[N+:15]([O-:17])=[O:16])([CH3:37])[CH2:35][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Reactant 5

HCID 7678Phenylacetone

HCID 433294Lithium Chloride

HCID 11186300Ethyl 4-iodo-3-nitrobenzoate

HCID 131730665Iodine magnesium

HCID 178478979HCID 178478979, compound

Product 1

HCID 69048245Ethyl 4-(1-hydroxy-1-methyl-2-phenylethyl)-3-nitrobenzoateYield 73%

Procedure

According to Example 2, the Grignard reagent 1e (freshly prepared via iodine-magnesium exchange[6] from ethyl-4-iodo-3-nitrobenzoate (353 mg, 1.10 mmol; 1.10 equiv) and PhMgCl.LiCl (0.95 M in THF; 1.13 mL, 1.07 mmol, 1.07 equiv) at −50° C.) was reacted with 1-phenyl-propan-2-one (201 mg; 1.00 mmol) in the presence of LaCl3.2LiCl (0.33 M; 3.03 mL, 1.00 mmol, 1.00 equiv). The crude product was purified by flash column chromatography (silica; pentane:Et2O, 19:1) to give the desired product as yellow oil (231 mg, 73%).

Workup

customThe crude product was purified by flash column chromatography (silica; pentane:Et2O, 19:1)

Sources & evidence

ORD record: ord-606d228428ba4377859179725bd7db7e
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470982B2

Reaction notes

Loading…