Sodium Bicarbonate → (Rac.) 4-(4-chloro-3-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

HRID 1443302Notes

Reaction equation

HRID 1443302 reaction equation
C([O:3][C:4](=O)[C:5]([C:21]([F:24])([F:23])[F:22])([OH:20])[CH2:6][C:7]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([F:17])[C:11]=1[O:18][CH3:19])([CH3:9])[CH3:8])C.[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O-])(O)=O.[Na+]>C(OCC)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]([CH3:9])([CH3:8])[CH2:6][C:5]([OH:20])([C:21]([F:24])([F:23])[F:22])[CH:4]=[O:3])=[C:11]([O:18][CH3:19])[C:12]=1[F:17]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 17989096(rac.) 4-(4-Chloro-3-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)-2-hydroxy-pentanoic acid ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 17989212(Rac.) 4-(4-chloro-3-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.00 g (2.59 mmol) of (rac.) 4-(4-chloro-3-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)-2-hydroxy-pentanoic acid ethyl ester is dissolved in 9.5 ml of diethyl ether and mixed in portions at 0° C. with 73.7 mg (1.94 mmol) of LiAlH4. Stirring is continued at 0° C., and a TLC is taken every quarter hour. After 40 minutes of stirring at 0° C., the reaction mixture is mixed drop by drop with 2.4 ml of saturated NaHCO3 solution while being cooled in an ice bath. It is stirred for 30 minutes while being cooled in an ice bath, and it is stirred vigorously overnight at room temperature. The precipitate is suctioned off, washed with ethyl acetate, and the filtrate is concentrated by evaporation in a rotary evaporator. After the residue is chromatographed on a Flashmaster, 560.2 mg is obtained. In this case, this is a 3:2 mixture of the aldehyde with the starting ester.

Workup

  1. customis continued at 0° C.
  2. waita TLC is taken every quarter hour
  3. stirringAfter 40 minutes of stirring at 0° C.
  4. temperaturewhile being cooled in an ice bath
  5. stirringIt is stirred for 30 minutes
  6. temperaturewhile being cooled in an ice bath
  7. stirringit is stirred vigorously overnight at room temperature
  8. washwashed with ethyl acetate
  9. concentrationthe filtrate is concentrated by evaporation in a rotary evaporator
  10. customAfter the residue is chromatographed on a Flashmaster
  11. custom560.2 mg is obtained

Sources & evidence

ORD record
ord-d052a8b298484bb5994e3a7798aba0ff
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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