Hydrochloric Acid → 2,3-Bis(2-hexynyl)-1,4-dipropylnaphthalene

HRID 600141Notes

Reaction equation

HRID 600141 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH:6]#[C:7][CH2:8][CH2:9][CH3:10].Br[CH2:12][C:13]1[C:22]([CH2:23]Br)=[C:21]([CH2:25][CH2:26][CH3:27])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1[CH2:28][CH2:29][CH3:30].[CH3:31]N1C(=O)N(C)CCC1.Cl>C1COCC1>[CH2:12]([C:13]1[C:22]([CH2:23][C:6]#[C:7][CH2:8][CH2:9][CH3:10])=[C:21]([CH2:25][CH2:26][CH3:27])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]=1[CH2:28][CH2:29][CH3:30])[C:4]#[C:3][CH2:2][CH2:1][CH3:31]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 123091-PentyneHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 154824292,3-Bis(bromomethyl)-1,4-dipropylnaphthaleneHCID 178418339Butyllithium

Product 1

HCID 113946772,3-Bis(2-hexynyl)-1,4-dipropylnaphthaleneYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyl lithium (7.6 ml, 19.1 mmols, 2.52 M) was added to a 30 ml THF solution of 1-pentyne (2.05 ml, 21.06 mmols) at −78° C., and the mixture was stirred at room temperature for an hour. 2,3-Bis(bromomethyl)-1,4-dipropylnaphthalene (1.91 g, 4.79 mmols) and DMPU (2.3 ml, 19.1 mmols) were added to the mixture at room temperature. After stirring for an hour, the mixture was treated with 3N HCl and extracted with hexane. The extract was then washed with sodium hydrogencarbonate aqueous solution and brine, followed by drying over anhydrous magnesium sulfate. Column chromatography was performed using silica gel as the packing material to give the title compound (1.66 g) as a white solid. The isolation yield was 93%

Workup

  1. stirringAfter stirring for an hour
  2. extractionextracted with hexane
  3. washThe extract was then washed with sodium hydrogencarbonate aqueous solution and brine
  4. dry with materialby drying over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-4d87af6bc4604984b31937c630c5e8d0
Source dataset
uspto-grants-2011_03
Patent number
US07901594B2

Reaction notes

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