Sodium Bicarbonate → 4-(2H-1,3-Benzodioxol-4-yl)-4-methyl-2-(trifluoromethyl)pentane-1,2-diol

HRID 1443160Notes

Reaction equation

HRID 1443160 reaction equation
C([O:3][C:4](=O)[C:5]([OH:23])([C:19]([F:22])([F:21])[F:20])[CH2:6][C:7]([C:10]1[C:18]2[O:17][CH2:16][O:15][C:14]=2[CH:13]=[CH:12][CH:11]=1)([CH3:9])[CH3:8])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)(O)[O-].[Na+]>C(OCC)C>[O:15]1[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([C:7]([CH3:9])([CH3:8])[CH2:6][C:5]([C:19]([F:20])([F:22])[F:21])([OH:23])[CH2:4][OH:3])[C:18]=2[O:17][CH2:16]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 17989248HCID 17989248, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 219488974-(2H-1,3-Benzodioxol-4-yl)-4-methyl-2-(trifluoromethyl)pentane-1,2-diolYield 61%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

12.5 g (36.03 mmol) of 4-(1,3-benzodioxol-4-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)-pentanoic acid ethyl ester is introduced into 430 ml of diethyl ether and mixed in portions with 2.05 g (54.1 mmol) of lithium aluminum hydride at 0° C. After stirring overnight at room temperature, the batch is carefully added to sodium bicarbonate solution. It is filtered by means of diatomaceous earth and extracted three times with ethyl acetate. The combined organic extracts are washed with brine, dried, and the solvent is spun off after the desiccant is filtered off. Chromatography of the residue on silica gel (mobile solvent:ethyl acetate/hexane) yields 6.7 g (61%) of the desired alcohol.

Workup

  1. filtrationIt is filtered by means of diatomaceous earth
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic extracts are washed with brine
  4. customdried
  5. filtrationis filtered off

Sources & evidence

ORD record
ord-cba4d7dae37a4d5aacd5c82195221bc4
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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