Hydrochloric Acid → HCID 11188975, compound

HRID 600136Notes

Reaction equation

HRID 600136 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:18]([CH2:19][CH2:20][CH3:21])=[C:17]([CH2:22][CH2:23][CH3:24])[C:16]([CH2:25][CH2:26][CH3:27])=[C:15]([CH2:28][CH2:29][CH3:30])[C:14]=1[CH2:31]Br.[CH3:33]N1C(=O)N(C)CCC1.Cl>C1COCC1>[CH2:12]([C:13]1[C:18]([CH2:19][CH2:20][CH3:21])=[C:17]([CH2:22][CH2:23][CH3:24])[C:16]([CH2:25][CH2:26][CH3:27])=[C:15]([CH2:28][CH2:29][CH3:30])[C:14]=1[CH2:31][C:6]#[C:7][CH2:8][CH2:9][CH3:10])[C:4]#[C:3][CH2:2][CH2:1][CH3:33]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 123091-PentyneHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 15482395HCID 15482395, compoundHCID 178418339Butyllithium

Product 1

HCID 11188975HCID 11188975, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyl lithium (9.7 ml, 15.56 mmols, 1.6 M) was added to a 30 ml THF solution of 1-pentyne (1.67 ml, 17.12 mmols) at −78° C., and the mixture was stirred at room temperature for an hour. 1,2-Bis(bromomethyl)-3,4,5,6-tetrapropylbenzene (1.68 g, 3.89 mmols) and DMPU (1.9 ml, 15.56 mmols) were added to the mixture at room temperature. After stirring for an hour, 3N HCl was added to terminate the reaction. The reaction mixture was 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 (1.520 g) as a white solid. The GC yield was 100% and the isolation yield was 97%

Workup

  1. stirringAfter stirring for an hour
  2. customto terminate
  3. customthe reaction
  4. extractionThe reaction mixture was extracted with hexane
  5. washThe extract was then washed with sodium hydrogencarbonate aqueous solution and brine
  6. dry with materialby drying over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-761e76c00de7463c9998549efe08e559
Source dataset
uspto-grants-2011_03
Patent number
US07901594B2

Reaction notes

Loading…