HCID 20481696, compound → HCID 20481701, compound

HRID 1648734Notes

Reaction equation

HRID 1648734 reaction equation
[C:1]([CH:4]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[C:15][CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:3])[CH3:2]>C(COC)OC.[Pd]>[C:1]([CH:4]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 20481696HCID 20481696, compound

Product 1

HCID 20481701HCID 20481701, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Ethyl 2-acetyl-9-tetrahydropyranyloxy-non-7-ynoate (25.9 g) was hydrogenated over 10% Pd/C (3 g) in dry dimethoxyethane (300 ml) at atmospheric pressure and room temperature. When hydrogen absorption was completed the mixture was filtered through kieselguhr and the filtrate was evaporated in vacuo. The residual oil was chromatographed on silica gel (600 g) using chloroform as eluant. Ethyl 2-acetyl-9-tetrahydropyranyloxy-nonanoate (20 g) was obtained as a colourless oil.

Workup

  1. customWhen hydrogen absorption
  2. filtrationwas filtered through kieselguhr
  3. customthe filtrate was evaporated in vacuo
  4. customThe residual oil was chromatographed on silica gel (600 g)

Sources & evidence

ORD record
ord-8ee1968cc67346e095457e8b543cc0a6
Source dataset
uspto-grants-1983_11
Patent number
US04413002

Reaction notes

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