HCID 67258438, compound → HCID 67259190, compound

HRID 2423377Notes

Reaction equation

HRID 2423377 reaction equation
[C:1]([C:9]1[CH:21]=[CH:20][C:12]([CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][C:15]2=[O:19])=[CH:11][CH:10]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>C(O)=O.[Pd].CO>[CH2:1]([C:9]1[CH:21]=[CH:20][C:12]([CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][C:15]2=[O:19])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 1

HCID 67258438HCID 67258438, compound

Product 1

HCID 67259190HCID 67259190, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 284Formic AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Several drops of formic acid and catalytic amount 5% Pd/C was added to a 25 mL flask charged with 10 mL methanol and 1.25 g (4.75 mmol) of 2-(4′-(oct-1-ynyl)benzyl)cyclopentanone (4). The reaction vessel was flushed with H2, three times, and then mounted with a H2 balloon. After two days under the hydrogen atmosphere, the reaction mixture was exposed to nitrogen, and then filtered through a pad of silica gel. The silica gel plug was washed with ethyl ether (2×25 mL) and the combined organic layers were concentrated to a crude product providing a light yellow oil (1.24 g, 98%).

Workup

  1. customThe reaction vessel was flushed with H2, three times
  2. filtrationfiltered through a pad of silica gel
  3. washThe silica gel plug was washed with ethyl ether (2×25 mL)
  4. concentrationthe combined organic layers were concentrated to a crude product

Sources & evidence

ORD record
ord-661fd8d1a5b5455a8be72a1db57479d4
Source dataset
uspto-grants-2011_06
Patent number
US07960588B2

Reaction notes

Loading…