(E)-N-methoxy-N-methyl-3-(3-cyclopentoxy-4-methoxyphenyl)-prop-2-enamide → (E)-4-(3-Cyclopentyloxy-4-methoxyphenyl)-3-buten-2-one

HRID 1377754Notes

Reaction equation

HRID 1377754 reaction equation
CON(C)[C:4](=[O:21])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:8]=1.[CH3:23][Li]>C1COCC1.CCOCC>[CH:16]1([O:15][C:9]2[CH:8]=[C:7](/[CH:6]=[CH:5]/[C:4](=[O:21])[CH3:23])[CH:12]=[CH:11][C:10]=2[O:13][CH3:14])[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 2

HCID 21193737(E)-N-methoxy-N-methyl-3-(3-cyclopentoxy-4-methoxyphenyl)-prop-2-enamideHCID 178418348HCID 178418348, compound

Product 1

HCID 21193738(E)-4-(3-Cyclopentyloxy-4-methoxyphenyl)-3-buten-2-oneYield 90%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-N-methoxy-N-methyl-3-(3-cyclopentoxy-4-methoxyphenyl)-prop-2-enamide (318 mg, 1.05 mmol) in 2.5 mL of THF cooled to 0° C. was added CH3Li (1.5 mL of 1.4M ether solution). The resulting solution was stirred for 5 min, diluted with ether and transferred to a separatory funnel. After washing with H2O, 1M H3PO4, and brine, the organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. Silica gel chromatography (3:1, hexanes:ethyl acetate) provided (E)-4-(3-cyclopentoxy-4-methoxyphenyl)-but-3-en-2-one as a white solid (234 mg, 90%). 1H-NMR (300 MHz): δ 2.38 (s, 3), 3.89 (s, 3), 6.59 (d, 1, J=16), 7.46 (d, 1, J=16).

Workup

  1. customtransferred to a separatory funnel
  2. washAfter washing with H2O, 1M H3PO4, and brine
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dc46e53e1527436ab8ee3255ea67a565
Source dataset
uspto-grants-1997_09
Patent number
US05665754

Reaction notes

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