Methanol → HCID 86663801, compound

HRID 2367714Notes

Reaction equation

HRID 2367714 reaction equation
[F:1][C:2]([F:12])([CH:6]([OH:11])[CH2:7][CH:8]([CH3:10])[CH3:9])[C:3]([OH:5])=[O:4].[CH3:13]O>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:1][C:2]([F:12])([CH:6]([OH:11])[CH2:7][CH:8]([CH3:10])[CH3:9])[C:3]([O:5][CH3:13])=[O:4]

Participants

4

Reactant 2

HCID 887MethanolHCID 57474515HCID 57474515, compound

Product 1

HCID 86663801HCID 86663801, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 521998p-Toluenesulfonic acid monohydrateCatalyst

Procedure

To a mixture of 28.11 g of Intermediate 1 (Example 1) and 280 g of methanol was added 0.6 g of p-toluenesulfonic acid monohydrate. With stirring in a nitrogen atmosphere, the mixture was heated under reflux for 8 hours. After cooling, the reaction mixture was concentrated to about 200 ml. The concentrate was poured into a saturated sodium hydrogen carbonate aqueous solution and extracted with ether. The ether solution was washed, dried, and concentrated, obtaining 21.8 g (yield 72%) of methyl 2,2-difluoro-3-hydroxy-5-methylhexanoate. This crude product had a sufficient purity as an intermediate and was ready for use in the subsequent step.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated to about 200 ml
  5. additionThe concentrate was poured into a saturated sodium hydrogen carbonate aqueous solution
  6. extractionextracted with ether
  7. washThe ether solution was washed
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-18d3a8929f07489ab962858cb67332c2
Source dataset
uspto-grants-2014_04
Patent number
US08697903B2

Reaction notes

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