Iodoethane → 3-(4-Benzyloxyphenyl)-2-ethoxypropanoic acid ethyl ester

HRID 1859942Notes

Reaction equation

[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH:18]([OH:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:25](I)[CH3:26]>CN(C)C(=O)C.C1(C)C=CC=CC=1>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH:18]([O:24][CH2:25][CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Sodium hydride (55% suspension in oil, 1.65 g) was added to a solution ethyl 3-(4-benzyloxyphenyl)lactate (10.30 g), which is the product of Reference example 1(b), in a mixture of N,N-dimethylacetamide (50 ml) and toluene (50 ml). The mixture was stirred at 40° C. for 30 minutes. To the reaction mixture were added ethyl iodide (3.3 ml) and toluene (5 ml). This mixture was stirred at 40° C. for 2 hours. At the end of this time the reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified via chromatography on a silica gel column using hexane/ethyl acetate=5/1 as the eluant to give the desired compound (5.50 g) as a syrup.

Workup

stirringThis mixture was stirred at 40° C. for 2 hours
customAt the end of this time the reaction mixture was partitioned between ethyl acetate and water
customThe ethyl acetate layer was separated
dry with materialdried over anhydrous magnesium sulfate
customevaporated under reduced pressure
customThe residue was purified via chromatography on a silica gel column

Sources & evidence

ORD record: ord-aee24221f1944d8c94ec03c74c99cfb8
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528525B1

Reaction notes

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