Water → HCID 86638989, compound

HRID 889282

Reaction equation

HRID 889282 reaction equation
[Li+].CC([N-][CH:6]([CH3:8])[CH3:7])C.[CH:9]([O:12][C:13](=[O:17])C(C)C)([CH3:11])[CH3:10].Br[CH2:19][C:20]#[CH:21].O>C1COCC1>[CH:9]([O:12][C:13](=[O:17])[C:6]([CH3:7])([CH3:8])[CH2:21][C:20]#[CH:19])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 12044Isopropyl isobutyrateHCID 2724682Lithium diisopropylamide

Product 1

HCID 86638989HCID 86638989, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of LDA (2M in THF, 5 mL) in THF (5 mL), at −78° C. is added a solution of isobutyric acid isopropyl ester (1.3 g, 10 mmol) in THF (3 mL) dropwise. After the addition is complete, the solution is slowly warmed to 0° C. and stirred there for 1 h. The temperature is reduced to −78° C. and a solution of 3-bromo-propyne (1.2 g, 10 mmol) in THF (3 mL) is added dropwise then the solution is allowed to warm 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 liquid.

Workup

  1. additionAfter the addition
  2. customis reduced to −78° C.
  3. temperatureto warm 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-80865e194f544a67b55e1f494e0cf682
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Linked notes

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