Methanol → HCID 15001601, compound

HRID 1775994Notes

Reaction equation

HRID 1775994 reaction equation
[F:1][C:2]([F:19])([CH:8]([O:13]C(=O)C(C)=C)[CH2:9][CH:10](C)C)[C:3]([O:5][CH2:6]C)=[O:4].CO.[C:22](=O)([O-])O.[Na+]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>[F:19][C:2]([F:1])([CH:8]([OH:13])[CH:9]([CH3:10])[CH3:22])[C:3]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 86663803HCID 86663803, compound

Product 1

HCID 15001601HCID 15001601, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 241BenzeneSolvent

Procedure

To a mixture of 50 g of Intermediate 2 (Example 2), 200 g of methanol and 250 g of benzene was added 0.3 g of p-toluenesulfonic acid monohydrate. With stirring in a nitrogen atmosphere, the mixture was heated under reflux for 20 hours. After cooling, the reaction mixture was poured into a saturated sodium hydrogen carbonate aqueous solution and extracted with hexane. The hexane solution was washed, dried, and concentrated, obtaining 45.78 g (yield 85%) of methyl 2,2-difluoro-3-hydroxy-4-methylpentanoate. 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 20 hours
  3. temperatureAfter cooling
  4. extractionextracted with hexane
  5. washThe hexane solution was washed
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cc2e4eedaa3a48cfa96c12765f789405
Source dataset
uspto-grants-2016_02
Patent number
US09261783B2

Reaction notes

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