Sodium hydride → HCID 18520718, compound

HRID 1368698Notes

Reaction equation

HRID 1368698 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[H-].[Na+].Br[CH2:11][C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20])=[O:13]>C1COCC1>[CH2:1]([O:7][CH2:11][C:12]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20])=[O:13])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699635-Hexen-1-olHCID 15738241HCID 15738241, compound

Product 1

HCID 18520718HCID 18520718, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

3,5 g (34 mmol) of 5-hexen-1-ol, dissolved in 25 ml of THF, are added dropwise to a suspension of 0.95 g (28 mmol) of NaH in 20 ml of THF. When the addition is complete, 4.8 g (23 mmol) of hex-5-enyl 2-bromoacetate, dissolved in 15 ml of THF, are added dropwise. The mixture is then refluxed overnight. When the reaction is complete, the mixture is left to cool and quenched with 2N HCl. After the phases have separated, the aqueous phase is extracted again with Et2O and twice with EtOAc. The combined organic phases are dried over Na2SO4, filtered and evaporated on a rotary evaporator. The crude product is purified on silica gel (cyclohexane/EtOAc=40:1; Rf=0.26), giving, as product, a colorless oil in a yield of 4.8 g (67% over 2 stages).

Workup

  1. additionWhen the addition
  2. additionare added dropwise
  3. temperatureThe mixture is then refluxed overnight
  4. waitthe mixture is left
  5. temperatureto cool
  6. customquenched with 2N HCl
  7. customAfter the phases have separated
  8. extractionthe aqueous phase is extracted again with Et2O and twice with EtOAc
  9. dry with materialThe combined organic phases are dried over Na2SO4
  10. filtrationfiltered
  11. customevaporated on a rotary evaporator
  12. customThe crude product is purified on silica gel (cyclohexane/EtOAc=40:1; Rf=0.26)
  13. customgiving, as product

Sources & evidence

ORD record
ord-669d76a9f9ea4ec4b75abf9b569201f6
Source dataset
uspto-grants-2003_06
Patent number
US06573391B1

Reaction notes

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