1-(4-Iodophenyl)ethan-1-one → HCID 11390977, compound

HRID 458224Notes

Reaction equation

HRID 458224 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][CH:5]=1)=[O:3].ClCC(OC(C1C=CC(I)=CC=1)C)=O>>[I:10][C:7]1[CH:8]=[CH:9][C:4]([C@@H:2]([OH:3])[CH3:1])=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 728691-(4-Iodophenyl)ethan-1-oneHCID 11616807HCID 11616807, compound

Product 1

HCID 11390977HCID 11390977, compound

Procedure

Starting from 4-iodophenyl methyl ketone, which is reduced to the racemic alcohol and converted to (±)-1-(4-iodophenyl)ethyl chloroacetate, the racemic ester is subjected to stereoselective enzyme hydrolysis. The remaining (S)-isomer of the ester is separated from the (R)-alcohol and transesterified to give (S)-1-(4-iodophenyl)ethanol (ee >98%) III.

Workup

  1. customThe remaining (S)-isomer of the ester is separated from the (R)-alcohol

Sources & evidence

ORD record
ord-eefb9ca0b5c747b6a04d6d1df2c24c00
Source dataset
uspto-grants-2007_03
Patent number
US07189859B2

Reaction notes

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