1-Iodopentane → HCID 14350139, compound

HRID 414285Notes

Reaction equation

HRID 414285 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:9][C:10]#[CH:11])=[CH:4][CH:3]=1.C[Li].I[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].CN(C)P(=O)(N(C)C)N(C)C>C1COCC1.C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:9][C:10]#[C:11][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 123351-IodopentaneHCID 12679HexamethylphosphoramideHCID 14350138HCID 14350138, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 14350139HCID 14350139, compoundYield 58.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To 2.2 g (63 mmol) of the silylacetylene of Example 2 dissolved in 50 ml of dry THF and cooled to -78° C. under argon was added dropwise 5.6 ml (7.0 mmol) of a 1.25M solution of methyl lithium in diethyl ether. Upon addition, the reaction was warmed to -10° C. and stirred at -10° C. for 30 min. Iodopentane (1.2 ml, 9.0 mmol) was then added followed by 5.0 ml of hexamethylphosphoric triamide (HMPA) whereupon the reaction mixture was warmed to R.T. and stirred overnight. The reaction was quenched with about 5.0 ml of H2O, then poured into hexane and washed 4× with H2O, and 1× with brine. The organic layer was dried (MgSO4) and the solvent removed to yield a dark red oil which was purified by medium pressure liquid chromotography (MPLC) eluting with hexane to yield 2.14 g of the titled product as a pale yellow oil.

Workup

  1. additionUpon addition
  2. temperaturethe reaction was warmed to -10° C.
  3. temperaturewas warmed to R.T.
  4. stirringstirred overnight
  5. customThe reaction was quenched with about 5.0 ml of H2O
  6. additionpoured into hexane
  7. washwashed 4× with H2O, and 1× with brine
  8. dry with materialThe organic layer was dried (MgSO4)
  9. customthe solvent removed
  10. customto yield a dark red oil which
  11. customwas purified by medium pressure liquid chromotography (MPLC)
  12. washeluting with hexane

Sources & evidence

ORD record
ord-151e700dd5454e4bbe39f0b19de59bbc
Source dataset
uspto-grants-1988_12
Patent number
US04791133

Reaction notes

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