Water → HCID 70374531, compound

HRID 2165010Notes

Reaction equation

HRID 2165010 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9]OC.[CH2:12]([Li])[CH2:13][CH2:14][CH3:15].[CH3:17][O:18][CH2:19][C:20]([C:22]1[CH:27]=CC=CC=1)=O.[OH2:28].[O:29]1[CH2:33]CCC1>CCCCCC.CCOCC>[Cl:1][C:2]1[C:3]([O:8][CH3:9])=[C:4]([C:14]([C:13]2[CH:12]=[CH:27][CH:22]=[CH:20][C:19]=2[O:18][CH3:17])([OH:28])[CH3:15])[CH:5]=[CH:6][C:7]=1[O:29][CH3:33]

Participants

8

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 776982-Methoxy-1-phenylethanoneHCID 5426241-Chloro-2-(methoxymethoxy)benzeneHCID 178418339Butyllithium

Product 1

HCID 70374531HCID 70374531, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

1-Chloro-2-methoxymethoxybenzene (20.0 g) was combined with 72.5 ml of 1.6M n-butyl lithium in hexane at 0° C. with stirring and allowed to react for 4 hours. A solution of 16.0 ml of 2-methoxyacetophenone in 20 ml of tetrahydrofuran was then added with stirring. After a short reaction period, water and ether were added and the ether layer was dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain an oil. This was purified by liquid chromatography, eluting with a 95:5 mixture of hexane and ethyl acetate, to obtain 6.67 g of the title compound as an oil. The assigned structure was consistent with the proton NMR spectrum.

Workup

  1. customto react for 4 hours
  2. stirringwith stirring
  3. additionwere added
  4. dry with materialthe ether layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customto obtain an oil
  8. customThis was purified by liquid chromatography
  9. washeluting with a 95:5 mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-1b5324bc6d1042029b904cbdae5c49fe
Source dataset
uspto-grants-1990_07
Patent number
US04938790

Reaction notes

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