1-(5-Chloro-2-ethoxy-3-iodo-4-methylphenyl)ethanone → 1-(5-Chloro-2-ethoxy-3-iodo-4-methylphenyl)ethanol

HRID 1499931Notes

Reaction equation

HRID 1499931 reaction equation
[Cl:1][C:2]1[C:3]([CH3:15])=[C:4]([I:14])[C:5]([O:11][CH2:12][CH3:13])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1>C(O)C>[Cl:1][C:2]1[C:3]([CH3:15])=[C:4]([I:14])[C:5]([O:11][CH2:12][CH3:13])=[C:6]([CH:8]([OH:10])[CH3:9])[CH:7]=1

Participants

3

Reactant 1

HCID 866668651-(5-Chloro-2-ethoxy-3-iodo-4-methylphenyl)ethanone

Product 1

HCID 866778481-(5-Chloro-2-ethoxy-3-iodo-4-methylphenyl)ethanolYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The desired compound was prepared according to the procedure of Example 212, step 4 (racemic mixture), using 1-(5-chloro-2-ethoxy-3-iodo-4-methylphenyl)ethanone instead of tert-butyl 3-(3-acetyl-5-chloro-6-cyano-2-ethoxyphenyl)azetidine-1-carboxylate as the starting material in 94% yield as a 96:4 mixture of enantiomers (RT=3.56 min and 4.28 min; Chiral Technologies ChiralPak AD-H column, 20×250 mm, 5 micron particle size, eluting with 5% ethanol in hexanes at 1 ml/min). LCMS for C11H13ClIO (M-(OH))+: m/z=323.0; Found: 322.9.

Sources & evidence

ORD record
ord-c1ba73e594bc418d82fb9f2cb4f33e5c
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

Loading…