Hydrochloric Acid → HCID 86615329, compound

HRID 1362520Notes

Reaction equation

HRID 1362520 reaction equation
[Cl:1][C:2]1[C:3]([O:24][CH3:25])=[C:4]([CH:8]([CH2:22][CH3:23])[CH2:9][C:10]2([C:18]([F:21])([F:20])[F:19])[O:14]C=N[CH:11]2[O:15]CC)[CH:5]=[CH:6][CH:7]=1.Cl>C1COCC1>[Cl:1][C:2]1[C:3]([O:24][CH3:25])=[C:4]([CH:8]([CH2:22][CH3:23])[CH2:9][C:10]([OH:14])([C:18]([F:21])([F:20])[F:19])[CH:11]=[O:15])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66969489HCID 66969489, compound

Product 1

HCID 86615329HCID 86615329, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 5-[2-(3-chloro-2-methoxyphenyl)butyl]-4-ethoxy-5-(trifluoromethyl)-4,5-dihydro-1,3-oxazole in THF (30 ml) is admixed with 2N HCl (10 ml). The mixture is stirred at 50-60° C. overnight. Following dilution with water (150 ml) and extraction with diethyl ether, the combined organic extracts are washed with water and brine and then dried and the solvent is removed on a rotary evaporator. Flash chromatography on silica gel (eluent toluene) gives 2.7 g (50%) of the desired compound as a racemic mixture of the two diastereomers. The 1H-NMR spectrum below describes the signals for the mixture:

Workup

  1. extractionwith water (150 ml) and extraction with diethyl ether
  2. washthe combined organic extracts are washed with water and brine
  3. customdried
  4. customthe solvent is removed on a rotary evaporator

Sources & evidence

ORD record
ord-8932daff39be40ae9f29826d7d7419c8
Source dataset
uspto-grants-2011_02
Patent number
US07880042B2

Reaction notes

Loading…