Triethylamine → 1-Cyclooctene

HRID 1193008Notes

Reaction equation

HRID 1193008 reaction equation
[FH:1].F.F.C(N(CC)CC)C.C(N(CC)CC)C.[CH:18]1(O)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>ClCCl>[F:1][CH:18]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[CH:18]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12766CyclooctanolHCID 175505N,N-Diethylethanamine trihydrofluoride

Product 2

HCID 136091-CycloocteneHCID 9793775Fluorocyclooctane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Procedure for the fluorination of alcohols (examples 74-84): To a suspension of the disubstituted aminodifluorosulfinium salt (1.5 mmol), triethylamine trihydrofluoride (326 μL, 2.0 mmol) and triethylamine (139 μL, 1.0 mmol) in dichloromethane (3.0 mL), at room temperature and under nitrogen, is added cyclooctanol (132 μl, 1.0 mmol). The reaction mixture is stirred for 19 h, then quenched with a 5% aqueous sodium bicarbonate solution, stirred for 15 min, and the resulting mixture was extracted using dichloromethane. The organic phases were combined, dried over magnesium sulfate and filtered through a pad of silica gel. Solvents were evaporated to provide fluorocyclooctane of admixed with cyclooctene as a clear oil (refer to the following table for yields and product distribution).

Workup

  1. customquenched with a 5% aqueous sodium bicarbonate solution
  2. stirringstirred for 15 min
  3. extractionthe resulting mixture was extracted
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through a pad of silica gel
  6. customSolvents were evaporated

Sources & evidence

ORD record
ord-b1cb8302f7114bb9b95480022f65839d
Source dataset
uspto-grants-2014_03
Patent number
US08680332B2

Reaction notes

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