Boron trifluoride etherate → Decalin

HRID 2306134Notes

Reaction equation

HRID 2306134 reaction equation
[CH2:1]1[C@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.FF.B(F)(F)F.CCOCC>C(#N)C>[CH2:9]1[CH:10]2[CH:5]([CH2:4][CH2:3][CH2:2][CH2:1]2)[CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 24524FluorineHCID 178420442HCID 178420442, compound

Product 1

HCID 7044DecalinYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
82 °C

Procedure

Using a similar procedure to that described above (Method 2), trans-decalin (3.0 g, 22 mmol), elemental fluorine (44 mmol), boron trifluoride etherate (3.1 g, 22 mmol), and anhydrous acetonitrile (120 cm3) gave, after heating (82° C.) and the work-up as detailed above, a crude product mixture which was distilled to give decalin (1.5 g, 11 mmol); bp 50° C./8 mmHg. The brown solid which remained gave, after recrystallisation, N-(trans-9-decalyl)acetamide (1.0 g, 45%, 49% conv.) as a white solid; spectral and physical data as described in Example 3.

Workup

  1. customgave
  2. distillationwas distilled

Sources & evidence

ORD record
ord-8c308e54727347b9aedf8c4c3dabf86f
Source dataset
uspto-grants-2002_08
Patent number
US06441232B1

Reaction notes

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