Diethyl Ether → HCID 3029755, compound

HRID 1253416Notes

Reaction equation

HRID 1253416 reaction equation
[OH:1][C:2]([CH2:7][CH3:8])([CH2:5][CH3:6])[C:3]#[CH:4].C([Li])CCC.[Br:14]Br.CCOCC>C1COCC1.O>[Br:14][C:4]#[C:3][C:2]([OH:1])([CH2:7][CH3:8])[CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 226983-Ethyl-1-pentyn-3-olHCID 24408BromineHCID 178418339Butyllithium

Product 1

HCID 3029755HCID 3029755, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

To a solution of 3-hydroxy-3-ethyl-1-pentyne (20 mmol) in dry THF (40 ml) at room temperature was added n-butyl-lithium (42 mmol, 1.6M in hexanes) during 10 minutes. After stirring for 30 minutes, the solution was cooled to −40° C. and a solution of bromine (1.13 ml, 3.52 g, 22 mmol) in dry THF (20 ml), also cooled to −40° C., was added, during 20 minutes, followed by re-heating to 25° C., during about 1 hour. Standard work-up after addition of ether and water (chromatography: 0% to 10% ether in petroleum ether) gave the title compound.

Workup

  1. additionwas added, during 20 minutes
  2. temperatureby re-heating to 25° C., during about 1 hour

Sources & evidence

ORD record
ord-27f5e233d7e3421380cb5557b844576a
Source dataset
uspto-grants-2013_06
Patent number
US08455466B2

Reaction notes

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