p-Toluenesulfonic acid → HCID 19937311, compound

HRID 1032919Notes

Reaction equation

HRID 1032919 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. washwashed with brine
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. 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-7aa0e2122a08404f848052d063812b1d
Source dataset
uspto-grants-1994_05
Patent number
US05308837

Reaction notes

Loading…