Water → HCID 15680402, compound

HRID 889277Notes

Reaction equation

HRID 889277 reaction equation
[Li+].CC([N-][CH:6]([CH3:8])[CH3:7])C.[CH2:9]([O:11][C:12](=[O:16])C(C)C)[CH3:10].Br[CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22].O>C1COCC1>[CH2:9]([O:11][C:12](=[O:16])[C:6]([CH3:7])([CH3:8])[CH2:22][CH2:21][CH2:20][CH:19]=[CH2:18])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 7342Ethyl isobutyrateHCID 707041-Pentene, 5-bromo-HCID 2724682Lithium diisopropylamide

Product 1

HCID 15680402HCID 15680402, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred solution of LDA (2M, 5 mL) in THF (5 mL), at −78° C., is added a solution of isobutyric acid ethyl ester (1.16 g, 10 mmol) in THF (3 mL) dropwise. After the addition, the solution is slowly warmed to RT and stirred for 20 min. The temperature is then reduced to −78° C. and a solution of 5-bromo-pent-1-ene (5 mL, 10 mmol) in THF (3 mL) is added dropwise. The solution is warmed to RT and stirred for 18 h. The mixture is poured into water and extracted with EtOAc. The organic layer is dried, filtered and the solvent is removed under reduced pressure. The residue is purified by flash chromatography using(hexane/EtOAc (10:1) as eluent to give the product as a colorless oil.

Workup

  1. additionAfter the addition
  2. customis then reduced to −78° C.
  3. temperatureThe solution is warmed to RT
  4. stirringstirred for 18 h
  5. extractionextracted with EtOAc
  6. customThe organic layer is dried
  7. filtrationfiltered
  8. customthe solvent is removed under reduced pressure
  9. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-52f93070b1c945f79a863a1a5b8a3a52
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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