Sodium Bicarbonate → HCID 15001600, compound

HRID 1775996Notes

Reaction equation

HRID 1775996 reaction equation
O.[C:2]1(C)C=CC(S(O)(=O)=O)=CC=1.[F:13][C:14]([F:23])([CH:18]([OH:22])[CH2:19][CH2:20][CH3:21])[C:15]([OH:17])=[O:16].C(=O)([O-])O.[Na+]>CO>[F:13][C:14]([F:23])([CH:18]([OH:22])[CH2:19][CH2:20][CH3:21])[C:15]([O:17][CH3:2])=[O:16]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 62397850HCID 62397850, compound

Product 1

HCID 15001600HCID 15001600, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A catalytic amount of p-toluenesulfonic acid monohydrate was added to a mixture of 75.5 g of Intermediate 4 in Example 4 and 200 g of methanol. With stirring in a nitrogen atmosphere, the reaction mixture was heated under reflux for 10 hours. After cooling, the reaction mixture was poured into a saturated sodium hydrogen carbonate aqueous solution and extracted with ethyl acetate. The ethyl acetate solution was washed, dried and concentrated, obtaining 63.0 g (yield 58%) of methyl 2,2-difluoro-3-hydroxyhexanoate. This crude product had a sufficient purity as an intermediate and was ready for use in the subsequent step.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 10 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate solution was washed
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-34b18a1aff714cc59eb2f76e46e1223c
Source dataset
uspto-grants-2016_02
Patent number
US09261783B2

Reaction notes

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