Sodium Bicarbonate → HCID 17989226, compound

HRID 1869413Notes

Reaction equation

HRID 1869413 reaction equation
C([O:3][C:4](=O)[C:5]([C:20]([F:23])([F:22])[F:21])([OH:19])[CH2:6][C:7]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([O:17][CH3:18])[CH:11]=1)(C)[CH3:8])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)(O)[O-].[Na+]>C(OCC)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([CH:7]([CH3:8])[CH2:6][C:5]([OH:19])([C:20]([F:23])([F:22])[F:21])[CH:4]=[O:3])=[CH:11][C:12]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 17989117HCID 17989117, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 17989226HCID 17989226, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

5.25 g (14.24 mmol) of (rac.) ethyl-4-(4-chloro-3-methoxyphenyl)-4-methyl-2-(trifluoromethyl)-2-hydroxy-pentanoate is dissolved in 53 ml of diethyl ether and mixed at 0° C. with 405.2 mg (10.68 mmol) of lithium aluminum hydride within 30 minutes. The reaction mixture is stirred for 1¼ more hours at 0° C. For hydrolysis, the mixture is mixed drop by drop with 12.5 ml of saturated sodium bicarbonate solution while being cooled in an ice bath. It is stirred vigorously for 30 minutes while being cooled in an ice bath and for 60 minutes at room temperature. The precipitate is suctioned off and washed with diethyl ether. The filtrate is concentrated by evaporation in a rotary evaporator, and the residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane). 3.29 g (71.2%) of the desired aldehyde, which still contains some starting ester and 54.7 mg of the corresponding diol, is isolated.

Workup

  1. customFor hydrolysis
  2. temperaturewhile being cooled in an ice bath
  3. stirringIt is stirred vigorously for 30 minutes
  4. temperaturewhile being cooled in an ice bath and for 60 minutes at room temperature
  5. washwashed with diethyl ether
  6. concentrationThe filtrate is concentrated by evaporation in a rotary evaporator
  7. customthe residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane)
  8. customis isolated

Sources & evidence

ORD record
ord-b6d88cf3353b4b76837aa815f47f5d1d
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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