Methanol → HCID 15406838, compound

HRID 443202Notes

Reaction equation

HRID 443202 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:22]#[CH:23])[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.O.O.O.[C:27]([O-:30])(=[O:29])C.[Na+].O.[CH3:33]O>[Cu](Cl)Cl.[Pd](Cl)Cl>[C:27]([C:23]#[C:22][C:15]1([C:9]2[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:8]=2)[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH2:16]1)([O:30][CH3:33])=[O:29]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 153920073-(3-Cyclopentyloxy-4-methoxyphenyl)-3-ethynylcyclohexan-1-oneHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 15406838HCID 15406838, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 24290Palladium ChlorideCatalyst

Procedure

3-(3Cyclopentyloxy-4-methoxyphenyl)-3-ethynylcyclohexan-1-one (0.30 g, 0.98 mmol) was dissolved in dry methanol (20 mL) and carbon monoxide was bubbled into the solution for 10 min. A mixture of copper (II) chloride (0.264 g, 1.96 mmol) and sodium acetate trihydrate (0.267 g, 1.96 mmol) was added, then trace palladium (II) chloride was added. After 2.5 h at room temperature, water was added and the methanol was evaporated The aqueous residue was extracted three times with ether, the combined extract was washed with brine, was dried (magnesium sulfate) and was evaporated. Purification by flash chromatography, eluting with 2:1 hexanes/ethyl acetate, provided a pale yellow oil. 1H NMR(400 MHz, CDCl3) δ7.0 (d, J=2.3Hz, 1H), 6.95 (dd, J=8.4, 2.3Hz, 1H), 6.84 (d, J=8.4Hz, 1H), 4.78 (m, 1H), 3.84 (s, 3H), 3.76 (s, 3H), 2.82 (d, J=25Hz, 1H), 2.78 (d, J=25Hz, 1H), 2.5-2.1 (m, 5H), 2.0-1.8 (m, 7H), 1.61 (m, 2H).

Workup

  1. customcarbon monoxide was bubbled into the solution for 10 min
  2. additionwas added
  3. additionwas added
  4. customthe methanol was evaporated The aqueous residue
  5. extractionwas extracted three times with ether
  6. extractionthe combined extract
  7. washwas washed with brine
  8. dry with materialwas dried (magnesium sulfate)
  9. customwas evaporated
  10. customPurification by flash chromatography
  11. washeluting with 2:1 hexanes/ethyl acetate
  12. customprovided a pale yellow oil

Sources & evidence

ORD record
ord-0f6a8178bf754aa6a17c46e188da12da
Source dataset
uspto-grants-1999_04
Patent number
US05892098

Reaction notes

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