Ethanone, 1-[3-methoxy-4-(methoxymethoxy)phenyl]- → HCID 59643063, compound

HRID 2251611Notes

Reaction equation

HRID 2251611 reaction equation
[Li][CH2:2]CCC.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:18](=O)[CH3:19])[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][O:16][CH3:17]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.CCCCCC>[C:18]([C:10]1[CH:11]=[CH:12][C:13]([O:14][CH2:15][O:16][CH3:17])=[C:8]([O:7][CH3:6])[CH:9]=1)([CH3:19])=[CH2:2]

Participants

6

Reactant 2

HCID 11356263Ethanone, 1-[3-methoxy-4-(methoxymethoxy)phenyl]-HCID 178418339Butyllithium

Product 1

HCID 59643063HCID 59643063, compound

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-80 °C

Procedure

A suspension of methyltriphenylphosphonium bromide (1.1 g, 3.09 mmol, 1.3 eq.) in 5 mL dry THF cooled to −80° C. was slowly treated with BuLi (1.94 mL of a 1.6 m solution in hexane, 1.3 eq.). To this yellow suspension a solution of 1-(3-methoxy-4-methoxymethoxy-phenyl)-ethanone (500 mg, 2.38 mmol, 1 eq.) in 5 mL dry THF was added and the reaction mixture was allowed to warm to r.t. where stirring was continued for 12 h. The suspension was filtered and the solvent was evaporated in vacuo. The crude product was purified using flash chromatography (silica gel, hexane/EtOAc 6:1) to yield the desired product as a color-less oil.

Workup

  1. temperatureto warm to r.t. where
  2. filtrationThe suspension was filtered
  3. customthe solvent was evaporated in vacuo
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-4f8aca4ed01348d1be726ba7af91abfe
Source dataset
uspto-grants-2008_01
Patent number
US07319101B2

Reaction notes

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