p-Toluenesulfonic acid → HCID 19937311, compound

HRID 36589Notes

Reaction equation

HRID 36589 reaction equation
[F:1][C:2]([F:23])([CH2:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22])[CH2:3][O:4]C1CCCCO1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[F:23][C:2]([F:1])([CH2:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22])[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 19937334HCID 19937334, compound

Product 1

HCID 19937311HCID 19937311, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,2-difluoro-3-phthalimido-1-tetrahydropyranyloxypropane (2 g, 6.15 mmol), paratoluene sulfonic acid (0.1 g) in absolute ethanol was stirred overnight at room temperature. Then the mixture was concentrated in vacuo, diluted with ethyl acetate and .,washed with brine. The organic phase was separated, dried over magnesium sulfate and concentrated in vacuo. The crude alcohol 2,2-difluoro-3-phthalimido-1-propanol (1.4 g) was used for the next step without further purification.

Workup

  1. concentrationThen the mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude alcohol 2,2-difluoro-3-phthalimido-1-propanol (1.4 g) was used for the next step without further purification

Sources & evidence

ORD record
ord-6e5d03d2f4b843e893a93aa80a544745
Source dataset
uspto-grants-1995_05
Patent number
US05416076

Reaction notes

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