Methanol → HCID 10755930, compound

HRID 1377751Notes

Reaction equation

HRID 1377751 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9](/[CH:15]=[C:16](\[CH3:20])/[C:17]([OH:19])=[O:18])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.OS(O)(=O)=O.[CH3:26]O>>[CH3:26][O:18][C:17](=[O:19])/[C:16](/[CH3:20])=[CH:15]/[C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 10707604HCID 10707604, compound

Product 1

HCID 10755930HCID 10755930, compoundYield 96%

Procedure

The carboxylic acid thus obtained (610 mg, 2.2 mmol) was dissolved in 10 mL of methanol and 3 drops of con. H2SO4 was added. The resulting solution was heated to reflux for 20 hr, cooled to room temperature, and partitioned between sat. NaHCO3 and CH2Cl2. The aqueous layer was extracted with CH2Cl2 (2×) and the combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure to an oil. Silica gel chromatography (4:1, hexanes:ethyl acetate) afforded (E)-methyl-3-(3-cyclopentoxy-4-methoxyphenyl)-2-methyl-prop-2-en-oate as a colorless solid (610 mg, 96%). 1H-NMR (300 MHz): d 2.15 (d, 3, J=1.2), 3.81 (s, 3), 3.88 (s, 3), 7.63 (s, 1). Anal. Calcd for C17H22O4 : C, 70.32; H, 7.64. Found: C, 70.44; H, 7.72.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 20 hr
  3. custompartitioned between sat. NaHCO3 and CH2Cl2
  4. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  5. dry with materialthe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure to an oil

Sources & evidence

ORD record
ord-32817cdb40ef472b9796dfd03b68a581
Source dataset
uspto-grants-1997_09
Patent number
US05665754

Reaction notes

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