Methanol → (E,E)-2,4-pentadecadien-6,9-diyn-1-yl tetrahydrothiophenium bromide

HRID 1106011Notes

Reaction equation

HRID 1106011 reaction equation
[Br:1][CH2:2]/[CH:3]=[CH:4]/[CH:5]=[CH:6]/[C:7]#[C:8][CH2:9][C:10]#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].CO.[S:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>>[Br-:1].[CH2:2]([S+:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)/[CH:3]=[CH:4]/[CH:5]=[CH:6]/[C:7]#[C:8][CH2:9][C:10]#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 3

HCID 887MethanolHCID 1127TetrahydrothiopheneHCID 12821661(E,E)-1-bromo-2,4-pentadecadien-6,9-diyne

Product 1

HCID 86738211(E,E)-2,4-pentadecadien-6,9-diyn-1-yl tetrahydrothiophenium bromide

Procedure

The (E,E)-1-bromo-2,4-pentadecadien-6,9-diyne (13.8 g) was dissolved in tetrahydrothiophene (14 mL) and then treated with an aqueous methanol solution (30 mL, 9:1). The two phase system was stirred at room temperature for 40 min (clear, one phase after 5-10 min) and then concentrated, 40° at 20 mmHg and room temperature at 0.5 mm for 10 min, to give the (E,E)-2,4-pentadecadien-6,9-diyn-1-yl tetrahydrothiophenium bromide as a semi-solid (24.2 g).

Workup

  1. concentrationconcentrated, 40° at 20 mmHg and room temperature at 0.5 mm for 10 min

Sources & evidence

ORD record
ord-13ed7a18b3c546bb8471463cc6b7f796
Source dataset
uspto-grants-1982_01
Patent number
US04311645

Reaction notes

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