Hexane → HCID 76528983, compound

HRID 2188322Notes

Reaction equation

HRID 2188322 reaction equation
[K].Cl[B:3]1[O:7][C:6]([CH3:9])([CH3:8])[C:5]([CH3:11])([CH3:10])[O:4]1.O1CCBO1.[CH3:17][CH2:18][CH2:19][CH2:20][CH2:21]C>>[CH2:21]([B:3]1[O:7][C:6]([CH3:9])([CH3:8])[C:5]([CH3:11])([CH3:10])[O:4]1)[CH:20]=[CH:19][CH:18]=[CH2:17]

Participants

5

Reactant 4

HCID 8058Hexane2×HCID 5462222PotassiumHCID 139254112-Chloro-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 172814838HCID 172814838, compound

Product 1

HCID 76528983HCID 76528983, compound

Conditions

Temperature
-78 °C

Procedure

About 0.55 moles of potassium piperylide is placed in a 2 liter, 3-neck flask with a mechanical stirrer, nitrogen bubbler, and a septum on the third neck. Approximately 340 ml of hexane is added and the flask is cooled to −78° C. in a dry ice/isopropyl alcohol bath. A dioxaborolane solution is prepared by dissolving 89.3 grams of 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.55 moles) in 750 ml of hexane. The dioxaborolane solution is added to the flask over about 2 hours while stirring. The mixture is stirred continuously overnight and is slowly warmed to room temperature. The flask contents are filtered and the solids are washed with about 250 ml of hexane. The resulting solution is concentrated by distilling off the hexane at atmospheric pressure. The product is 2-(2,4-pentadienyl)4,4,5,5-tetramethyl-1,3,2-dioxaborolane which is then vacuum distilled at 58° C. and 3 mbar.

Workup

  1. stirringThe mixture is stirred continuously overnight
  2. temperatureis slowly warmed to room temperature
  3. filtrationThe flask contents are filtered
  4. washthe solids are washed with about 250 ml of hexane
  5. concentrationThe resulting solution is concentrated
  6. distillationby distilling off the hexane at atmospheric pressure
  7. distillationvacuum distilled at 58° C.

Sources & evidence

ORD record
ord-b6449f8dcb904ddb99c986ca583e0adb
Source dataset
uspto-grants-2002_06
Patent number
US06410764B1

Reaction notes

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