Triethylamine → HCID 12106515, compound

HRID 1791976Notes

Reaction equation

HRID 1791976 reaction equation
[CH2:1]([Sn](CCCC)(CCCC)CCCC)[CH:2]=[CH2:3].[B:17]([Cl:20])(Cl)Cl.[CH2:21]([NH:24][CH2:25][CH:26]=[CH2:27])[CH:22]=[CH2:23].C(N(CC)CC)C>CCCCCC>[CH2:3]([B:17]([Cl:20])[N:24]([CH2:25][CH:26]=[CH2:27])[CH2:21][CH:22]=[CH2:23])[CH:2]=[CH2:1]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25135Boron TrichlorideHCID 31279DiallylamineHCID 90628Allyltributylstannane

Product 1

HCID 12106515HCID 12106515, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of allyltributyltin (62.2 g, 0.19 mol) in 50 mL of hexane was added dropwise to a solution of BCl3 (24.8 g, 0.21 mol) in 120 mL of hexane at −78° C. After the reaction mixture was stirred at −78° C. for 1 hour, it was allowed to warm to 25° C. for 2 hours followed by recooling to −78° C. Then diallylamine (23.5 mL, 0.19 mol) was added dropwise followed by triethylamine (26.7 mL, 0.19 mol). The mixture was stirred for 12 hours while it slowly warmed to 25° C. The solvent was removed under reduced pressure and the product (33.1 g, 95 percent) was obtained by distillation (bp=38° C. at 0.1 torr).

Workup

  1. temperatureto warm to 25° C. for 2 hours
  2. customby recooling to −78° C
  3. stirringThe mixture was stirred for 12 hours while it
  4. temperatureslowly warmed to 25° C
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-976d026fc2624c0ab091f731d189ba3f
Source dataset
uspto-grants-2006_07
Patent number
US07074865B2

Reaction notes

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