HCID 71185318, compound → HCID 71185457, compound

HRID 926413Notes

Reaction equation

HRID 926413 reaction equation
[Li][CH3:2].[CH3:3][C:4]1[C:9]([CH3:11])([CH3:10])[C:8](=[O:12])[CH2:7][C:6]([CH3:14])([CH3:13])[C:5]=1[C:15]([O:17][CH3:18])=[O:16]>C1COCC1>[OH:12][C:8]1([CH3:2])[CH2:7][C:6]([CH3:13])([CH3:14])[C:5]([C:15]([O:17][CH3:18])=[O:16])=[C:4]([CH3:3])[C:9]1([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 71185318HCID 71185318, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 71185457HCID 71185457, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of CeCl3 (1.51 equiv.) in THF (75 ml) was stirred at room temp for 1 hour. The suspension was cooled down to −78° C., MeLi (1.50 equiv., 1.46M in Et2O) was slowly added over 10 minutes, followed by the addition of a solution of (2a) (20.31 mmol) in THF (15 ml). After 30 minutes, the mixture was allowed to warm to 0° C. and quenched by adding NH4Cl and ice. The mixture was extracted with Et2O and the organic layers were washed with water, saturated bicarbonate solution, and brine. After drying with MgSO4, the solution was concentrated and distilled (125° C., 0.1 mbar). Yield 99%.

Workup

  1. temperatureto warm to 0° C.
  2. customquenched
  3. additionby adding NH4Cl and ice
  4. extractionThe mixture was extracted with Et2O
  5. washthe organic layers were washed with water, saturated bicarbonate solution, and brine
  6. dry with materialAfter drying with MgSO4
  7. concentrationthe solution was concentrated
  8. distillationdistilled (125° C., 0.1 mbar)

Sources & evidence

ORD record
ord-3a36ef6f429146a8bcb764c6bf7826cb
Source dataset
uspto-grants-2016_03
Patent number
US09284514B2

Reaction notes

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