1,6-Dibromohexane → HCID 22228022, compound

HRID 1032800Notes

Reaction equation

HRID 1032800 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].Br[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]Br.CN1CCCN(C)C1=[O:22]>O1CCCC1>[C:7]1([CH3:1])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:3]([O:22][CH:8]([CH3:9])[CH3:7])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 123681,6-DibromohexaneHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 178418339Butyllithium

Product 1

HCID 22228022HCID 22228022, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3.33 g of 3,4-bis-(tetrahydropyranyl-2'-oxy)-phenylacetylene in 20 ml of absolute tetrahydrofuran were added dropwise over 45 minutes at -78° to -70° C., while stirring in an atmosphere of dry nitrogen, 6.9 ml of n-butyllithium solution, and after one hour stirring at the same temperature 5.1 ml of 1,6-dibromohexane followed by 7 ml of absolute 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone were added dropwise. The mixture was stirred for 20 hours, allowed to warm to 0° C. and then worked up as described in Example 5e. By column chromatography with toluene/diisopropyl ether (10:1) 3.55 g of the title compound were obtained.

Workup

  1. additionwere added dropwise

Sources & evidence

ORD record
ord-6b955bab4a7c4bad97e43f89861f0d96
Source dataset
uspto-grants-1990_09
Patent number
US04959391

Reaction notes

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