1,1,1,3,3,3-Hexafluoro-2-propanol → HCID 57786782, compound

HRID 1969123Notes

Reaction equation

HRID 1969123 reaction equation
[CH:1]([N:14]1[CH2:17][CH:16]([O:18]S(C)(=O)=O)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:23][C:24]([F:32])([F:31])[CH:25](O)[C:26]([F:29])([F:28])[F:27]>>[CH:1]([N:14]1[CH2:17][CH:16]([O:18][CH:25]([C:26]([F:29])([F:28])[F:27])[C:24]([F:32])([F:31])[F:23])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanolHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 57786782HCID 57786782, compoundYield 25%

Procedure

A solution of methanesulfonic acid 1-benzhydryl-azetidin-3-yl ester (0.194 g, 0.61 mmol) in 2 mL of hexafluoroisopropanol in a sealed tube was stirred at 100° C. for 14 h, then concentrated. The residue was partitioned between 5 mL of ethyl acetate and 5 mL of a 10% NaOH solution. The organic layer was sequentially washed with 5 mL of water and 5 mL of a sat. aq. NaCl solution; dried over MgSO4, filtered and concentrated to an orange-yellow oil. Column chromatography (0-<20% EtOAc/hexanes) afforded 0.059 g (25%) of 1-benzhydryl-3-(2,2,2-trifluoro-1-trifluoromethyl-ethoxy)-azetidine as a colorless oil.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between 5 mL of ethyl acetate and 5 mL of a 10% NaOH solution
  3. washThe organic layer was sequentially washed with 5 mL of water and 5 mL of a sat. aq. NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to an orange-yellow oil

Sources & evidence

ORD record
ord-f05721f30cd0453eb1ac37f532d3f3e1
Source dataset
uspto-grants-2013_04
Patent number
US08426441B2

Reaction notes

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