HCID 21866891, compound → HCID 21866851, compound

HRID 857202Notes

Reaction equation

HRID 857202 reaction equation
[CH3:1][C:2]([O:9][CH2:10][CH2:11][CH2:12][C:13]#[C:14][CH2:15][O:16]C1CCCCO1)([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4]>C(O)C>[OH:16][CH2:15][C:14]#[C:13][CH2:12][CH2:11][CH2:10][O:9][C:2]([CH3:1])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

3

Reactant 1

HCID 21866891HCID 21866891, compound

Product 1

HCID 21866851HCID 21866851, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
57.5 °C

Procedure

Ethyl 2-methyl-2-[6-(tetrahydro-2H-pyran-2-yloxy)-4-hexynyloxy]propionate (3.72 g) was dissolved in 37 ml of ethanol, and 15.372 mg of Amberlyst® was added thereto and the mixture was stirred for 1 hour at 55-60° C. After cooling, the mixture was filtrated and the filtrate was concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=9:1-3:1) to provide 1.98 g of the objective compound as pale yellow oil.

Workup

  1. addition15.372 mg of Amberlyst® was added
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtrated
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=9:1-3:1)

Sources & evidence

ORD record
ord-6d4c907ecdcd4822a2c0cd6c8e3bc096
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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