4-Fluorobenzaldehyde → (S)-2-[(4-Fluorobenzylidene)-amino]-4-methylpentan-1-ol

HRID 2223548Notes

Reaction equation

HRID 2223548 reaction equation
[NH2:1][C@H:2]([CH2:7][OH:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1>C1C=CC=CC=1>[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[N:1][C@@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[CH2:7][OH:8])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 680234-FluorobenzaldehydeHCID 111307L-Leucinol

Product 1

HCID 57515778(S)-2-[(4-Fluorobenzylidene)-amino]-4-methylpentan-1-ol

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of (L)-leucinol (1.13 g, 9.67 mmol) and 4-fluorobenzaldehyde (1.20 g, 9.67 mmol) was dissolved in benzene (30 mL) and heated at reflux for 1 hour, using a Dean-Stark apparatus to remove water. (S)-2-[(4-Fluorobenzylidene)-amino]-4-methylpentan-1-ol was isolated by concentration in vacuo, and was used immediately without further purification.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. customto remove water

Sources & evidence

ORD record
ord-694c44aea7c540f98c6a8ad6b54bb4c4
Source dataset
uspto-grants-2008_05
Patent number
US07375134B2

Reaction notes

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