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

HRID 420637Notes

Reaction equation

HRID 420637 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 with 73.7 mg (1.94 mmol) of LiAlH4 at 0° C. Stirring is continued at 0° C. and a TLC is drawn off every one-quarter hour. After forty 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 vigorously stirred for 30 minutes while being cooled in an ice bath and 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 chromatography of the residue on a Flashmaster, 560.2 mg is obtained. This is a 3:2 mixture of the aldehyde with the starting ester.

Workup

  1. customis continued at 0° C.
  2. waita TLC is drawn off every one-quarter hour
  3. stirringAfter forty minutes of stirring at 0° C.
  4. temperaturewhile being cooled in an ice bath
  5. stirringIt is vigorously stirred for 30 minutes
  6. washwashed with ethyl acetate
  7. concentrationthe filtrate is concentrated by evaporation in a rotary evaporator
  8. customAfter chromatography of the residue on a Flashmaster, 560.2 mg is obtained

Sources & evidence

ORD record
ord-9e7d2bbcfcd544e4bb311f1d21bf62d4
Source dataset
uspto-grants-2012_01
Patent number
US08097627B2

Reaction notes

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