Diethyl Ether → HCID 66921219, compound

HRID 1487285Notes

Reaction equation

HRID 1487285 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=O)[CH:10]2[O:14][CH2:15][C:16]([O:19][CH3:20])([O:17][CH3:18])[CH:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21]C([O-])(C)C.[K+].C(OCC)C>C1COCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[CH2:21])[CH:10]2[O:14][CH2:15][C:16]([O:17][CH3:18])([O:19][CH3:20])[CH:9]12)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 23665647Potassium tert-butoxideHCID 66921243HCID 66921243, compound

Product 1

HCID 66921219HCID 66921219, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

The keto compound 1e (1.10 g, 3.83 mmol) was dissolved in dry THF (30 mL) and the solution was cooled to 0° C. A solution of methyl triphenylphosphonium bromide (4.0 g, 11.2 mmol) and KOtBu (1.17 g, 10.5 mmol) in dry THF (40 mL) was added in 3 aliquots with 2 hours interval. After 6 hrs the solution was poured into a separatory funnel with diethyl ether (70 mL) and extracted with 10% citric acid (aq)(2*40 mL). The organic phase was washed with saturated aqueous NaHCO3 (40 mL), dried with Na2SO4, filtered and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography (heptane: ethyl acetate 4:1) which gave the title compound (524 mg, 48%)

Workup

  1. extractionextracted with 10% citric acid (aq)(2*40 mL)
  2. washThe organic phase was washed with saturated aqueous NaHCO3 (40 mL)
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated in vacuo
  6. customThe crude product was purified by flash chromatography (heptane: ethyl acetate 4:1) which

Sources & evidence

ORD record
ord-ec1be30323d843dfa392dadb4e06e34c
Source dataset
uspto-grants-2016_08
Patent number
US09428517B2

Reaction notes

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