Boron trifluoride etherate → Decalin

HRID 2306133Notes

Reaction equation

HRID 2306133 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 178420443HCID 178420443, compound

Product 1

HCID 7044DecalinYield 31.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
82 °C

Procedure

Using a similar procedure to that described above (Method 2), cis-decalin (2.2 g, 16 mmol), elemental fluorine (65 mmol), boron trifluoride etherate (2.3 g, 16 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 (0.7 g, 5 mmol); bp 55° C./10 mmHg. The brown solid which remained gave, after recrystallisation, N-(trans-9-decalyl)acetamide (0.8 g, 49%, 67% conv.) as a white solid; mp 183-184° C. (from acetonitrile) (Found C, 73.6; H, 10.9; N, 7.3. C12H21NO requires: C, 73.8; H, 10.9; N, 7.2%); δH (400 MHz) 0.85-1.68 (18 H, m), 2.57 (1 H, s), 2.62 (1 H, s), 4.89 (1 H, br s, NH); δC (101 MHz) 21.6 (s, CH2), 24.6 (s, CH3), 26.1 (s, CH2), 28.6 (s, CH2), 34.4 (s, CH2), 45.2 (s, CH), 55.9 (CNHCO), 169.2 (s, CO); m/z (EI+) 195 (M+, 1%), 152 (18), 136 (100), 121 (141).

Workup

  1. customgave
  2. distillationwas distilled

Sources & evidence

ORD record
ord-c34f185ef749458ab0f75613d7a4cbbb
Source dataset
uspto-grants-2002_08
Patent number
US06441232B1

Reaction notes

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