HCID 57989255, compound → HCID 57989384, compound

HRID 471325Notes

Reaction equation

HRID 471325 reaction equation
[CH3:1][C:2]([CH3:22])([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1)/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6]>[Pd]>[CH3:22][C:2]([CH3:1])([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1)[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

3

Reactant 1

HCID 57989255HCID 57989255, compound

Product 1

HCID 57989384HCID 57989384, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of (E)-Ethyl 4,4-dimethyl-9-(tetrahydro-2H-pyran-2-yloxy)non-2-enoate (example 285, step d) (0.89 g) in IMS (industrial methylated spirits) (10 mL) was treated with palladium on carbon (spatula tip) under nitrogen then the flask was purged with hydrogen (×3) then stirred under an atmosphere of hydrogen overnight. A further portion of palladium on carbon was added and hydrogenation resumed for a further 24 hours. The catalyst was removed by filtration through diatomaceous earth and the filtrate was evaporated to afford the subtitled compound as a colourless oil. Yield 0.86 g.

Workup

  1. customthe flask was purged with hydrogen (×3)
  2. additionA further portion of palladium on carbon was added
  3. waithydrogenation resumed for a further 24 hours
  4. customThe catalyst was removed by filtration through diatomaceous earth
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-691dc4eafe644bcb9c0d435b4ed10fec
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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