Hydrochloric Acid → Deca-2,8-diyne-1,10-diol

HRID 1648531

Reaction equation

HRID 1648531 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[CH:8].[Li]CCCC.C=[O:15].Cl.C1C[O:20][CH2:19][CH2:18]1>CCOCC>[CH2:1]([OH:15])[C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[C:18][CH2:19][OH:20]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 700991,7-OctadiyneHCID 178418339Butyllithium

Product 1

HCID 14168564Deca-2,8-diyne-1,10-diolYield 50%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

2.12 g of commercially available 1,7 octadiyne (20.0 mmol) was first combined with 80 mL of Et2O and 30 mL of THF. The solution was cooled to -78° C. and treated with 15.6 mL (42 mmol, 2.7M) of BuLi. After 0.5 hr at this temperature, 4.8 g of paraformaldehyde (160 mmol) was added and stirred for a further 2.0 hr at 0° C. At 10% soln. of aqueous HCl was added and the crude product extracted into diethyl ether. Treatment of the ether extracts with sat. NaHCO3 and brine, followed by solvent removal and column chromatography (60:40 EtOAc: Hexane) gave pure deca-2,8-diyne-1,10-diol in 50% yield.

Workup

  1. extractionthe crude product extracted into diethyl ether
  2. customfollowed by solvent removal and column chromatography (60:40 EtOAc: Hexane)

Sources & evidence

ORD record
ord-b19e511fb21e461cbc8699424a744fa4
Source dataset
uspto-grants-1995_07
Patent number
US05436361

Linked notes

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