Hydrochloric Acid → HCID 10955105, compound

HRID 2308399Notes

Reaction equation

HRID 2308399 reaction equation
[CH2:1]([Mg]Br)[C:2]#[CH:3].Br[CH2:7]/[CH:8]=[C:9](\[CH3:19])/[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].Cl>Cl[Cu].C(OCC)C>[CH3:19]/[C:9](/[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:8]\[CH2:7][CH2:3][C:2]#[CH:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11010750HCID 11010750, compoundHCID 178455849HCID 178455849, compound

Product 1

HCID 10955105HCID 10955105, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A diethyl ether solution (100 ml) of propargyl bromide (22.4 g, 190 mmols) was added dropwise to magnesium (5.20 g, 210 mmols) and HgCl2 (360 mg, 1.33 mmols) to obtain propargyl magnesium bromide (Grignard reagent). CuCl (200 mg, 2.02 mmols) was added to this Grignard reagent, and the resulting solution was ice-cooled. After a diethyl ether (100 ml) solution of (E)-1-bromo-3-methyl-2-dodecene (4′) (18.8 g, 72.0 mmols) was added dropwise, the mixture was stirred for 3 hours at 0° C. The reaction mixture was poured into ice water, acidified with diluted hydrochloric acid, and extracted several times with diethyl ether. The organic layers were combined, and washed with water and a saturated aqueous solution of sodium chloride. A small amount of allene type impurities was removed by silica gel column chromatography (elution with hexane) to obtain pure (E)-6-methyl-5-pentadecen-1-yne (5′) (12.7 g, 80%).

Workup

  1. temperaturecooled
  2. extractionextracted several times with diethyl ether
  3. washwashed with water
  4. customA small amount of allene type impurities was removed by silica gel column chromatography (elution with hexane)

Sources & evidence

ORD record
ord-fd0faea8f0de485a9795b68af580d301
Source dataset
uspto-grants-2004_12
Patent number
US06835846B2

Reaction notes

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