(+/-)-Methyl {4-[2,4-bis(methoxymethoxy)phenyl]cyclohexylidene}acetate → HCID 178497879, compound

HRID 585665Notes

Reaction equation

HRID 585665 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:20][CH2:19][C:18](=[CH:21][C:22]([O:24][CH3:25])=[O:23])[CH2:17][CH2:16]1>[Pd].C(O)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[C@H:15]1[CH2:16][CH2:17][C@H:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:19][CH2:20]1

Participants

4

Reactant 1

HCID 91541557(+/-)-Methyl {4-[2,4-bis(methoxymethoxy)phenyl]cyclohexylidene}acetate

Product 1

HCID 178497879HCID 178497879, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a round bottomed flask equipped with magnetic stirrer was added (±)-methyl {4-[2,4-bis(methoxymethoxy)phenyl]cyclohexylidene}acetate (1.13 g, 3.23 mmol) and ethanol (50 ml). To the stirred solution was added palladium (catalytic amount, 10% on activated carbon) in one portion. The reaction vessel was evacuated and placed under an atmosphere of hydrogen. This process was repeated for 10 cycles before leaving under a hydrogen atmosphere and then stirred vigorously for 17 hr. The reaction mixture was filtered through celite, washing with ethanol and the filtrate was evaporated to dryness, furnishing the title compound (1.13 g, 99%) as a colourless oil and a mixture of diastereoisomers. δH(CD3OD) 1.53 (2H, m), 1.62-1.78 (2H, m), 1.87 (4H, m), 2.93 (1H, m), 3.47 (3H, s), 3.51 (3H, s), 3.71 and 3.72 (3H, s), 5.16 and 5.17 (2H, s), 5.22 and 5.23 (2H, s), 6.66 and 6.68 (1H, d), 6.79 and 6.80 (1H, s), 7.12 and 7.15 (1H, d).

Workup

  1. customTo a round bottomed flask equipped with magnetic stirrer
  2. customThe reaction vessel was evacuated
  3. custombefore leaving under a hydrogen atmosphere
  4. filtrationThe reaction mixture was filtered through celite
  5. washwashing with ethanol
  6. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-dd40ee033f7b4a1c916f33dcdb0d0d6b
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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