Pyridine → 1-Bromo-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaene

HRID 1645933Notes

Reaction equation

HRID 1645933 reaction equation
P(Br)(Br)[Br:2].[CH3:5][C:6]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:55])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:54])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:53])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:52])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:51])[CH2:30][CH2:31][CH:32]=[C:33]([CH3:50])[CH2:34][CH2:35][CH:36]=[C:37]([CH3:49])[CH2:38][CH2:39][CH:40]=[C:41]([CH3:48])[CH2:42][CH2:43][CH:44]=[C:45]([CH3:47])[CH3:46])=[CH:7][CH2:8]O.N1C=CC=CC=1>CCCCCC>[Br:2][CH2:8][CH:7]=[C:6]([CH3:5])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:55])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:54])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:53])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:52])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:51])[CH2:30][CH2:31][CH:32]=[C:33]([CH3:50])[CH2:34][CH2:35][CH:36]=[C:37]([CH3:49])[CH2:38][CH2:39][CH:40]=[C:41]([CH3:48])[CH2:42][CH2:43][CH:44]=[C:45]([CH3:47])[CH3:46]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 534397713,7,11,15,19,23,27,31,35,39-Decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-ol

Product 1

HCID 543963751-Bromo-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaeneYield 168.8%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Conditions

Temperature
10 °C

Procedure

Under an atmosphere of argon, a solution of phosphorus tribromide (8.32 g, 30.7 mmol) in 27 ml of n-hexane was added in dropwise to a mixture of 3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaen-1-ol (40 g, 57.3 mmol) and pyridine (1.92 ml, 23.8 mmol) in 587 ml of n-hexane at the temperature below 10° C. The solution was stirred at 10° C. for an hour, allowed to warm slowly from 10° to 20° C., stirred at 20°-25° C. for an hour and poured into cracked ice with stirring. The resulting precipitate was filtered off and the filtrate was extracted with n-hexane. The organic layer was washed with 5% sodium bicarbonate aqueous solution, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to dryness to afford 39.5 g (90.4%) of the desired compound, as a yellow oil.

Workup

  1. temperatureto warm slowly from 10° to 20° C.
  2. stirringstirred at 20°-25° C. for an hour
  3. additionpoured into cracked ice
  4. stirringwith stirring
  5. filtrationThe resulting precipitate was filtered off
  6. extractionthe filtrate was extracted with n-hexane
  7. washThe organic layer was washed with 5% sodium bicarbonate aqueous solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo to dryness

Sources & evidence

ORD record
ord-b5cd68dcde544fe7a6118fe411b76b58
Source dataset
uspto-grants-1993_01
Patent number
US05177102

Reaction notes

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