1-Hexyne → HCID 178442536, compound

HRID 1198325Notes

Reaction equation

HRID 1198325 reaction equation
[H-].[CH2:2]([Al+]CC(C)C)C(C)C.[CH:11]#[C:12][CH2:13][CH2:14][CH2:15]C.[CH2:17]([Li])[CH2:18][CH2:19][CH3:20].[F:22][C:23]1[C:32]([F:33])=[C:31]([C@H:34]2[CH2:39][CH2:38][C@H:37]([CH2:40][CH2:41][CH2:42]CC)CC2)[CH:30]=[CH:29][C:24]=1[CH:25](Br)[O:26][CH3:27]>CCCCCC.O1CCCC1>[F:33][C:32]1[C:23]([F:22])=[C:24]([C@H:29]2[CH2:20][CH2:19][C@H:18]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:17][CH2:30]2)[C:25]([O:26][CH3:27])=[CH:2][C:31]=1[CH2:34]/[CH:39]=[CH:38]/[CH2:37][CH2:40][CH2:41][CH3:42]

Participants

7

Reactant 4

HCID 127321-HexyneHCID 21225700DiisobutylaluminumhydrideHCID 178418339ButyllithiumHCID 178444300HCID 178444300, compound

Product 1

HCID 178442536HCID 178442536, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent3×

Procedure

10 ml of a 20% solution of diisobutylaluminium hydride in hexane are added to a solution of 0.01 mol of 1-hexyne and 5 ml of hexane and the mixture is heated at 50° for 3 hours. It is then cooled to 25°, 6.3 ml of a 15% solution of butyllithium in hexane are added dropwise, after 30 minutes 0.01 mol of 2,3-difluoro-4-(trans-4-pentylcyclohexyl)-methoxybenzyl bromide, dissolved in 15 ml of tetrahydrofuran, are added dropwise and the mixture is heated under reflux for 12 hours. Working up gives 2,3-difluoro-4-(trans-4-pentylcyclohexyl)-methoxy-trans-hept-2-enylbenzene.

Workup

  1. temperaturethe mixture is heated at 50° for 3 hours
  2. temperatureIt is then cooled to 25°
  3. additionare added dropwise
  4. temperaturethe mixture is heated
  5. temperatureunder reflux for 12 hours

Sources & evidence

ORD record
ord-0ad5fd52a0814aa69ebdc3b27e28e809
Source dataset
uspto-grants-1994_01
Patent number
US05279764

Reaction notes

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