Methane → Methyl 3-[3-(methyloxy)propyl]-1-naphthalenecarboxylate

HRID 337563Notes

Reaction equation

HRID 337563 reaction equation
[CH3:1][O:2][CH2:3]/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]([C:16]([O:18][CH3:19])=[O:17])[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2.C>CO.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([C:16]([O:18][CH3:19])=[O:17])[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

5

Reactant 2

HCID 297MethaneHCID 67062152Methyl 3-[(1E)-3-(methyloxy)-1-propen-1-yl]-1-naphthalenecarboxylate

Product 1

HCID 66896160Methyl 3-[3-(methyloxy)propyl]-1-naphthalenecarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 3-[(1E)-3-(methyloxy)-1-propen-1-yl]-1-naphthalenecarboxylate (1 eq.) from the previous step and 10% w/w palladium over charcoal (0.1 eq.) were suspended in MeOH (0.08 M). The vessel was then evacuated and purged with H2. Under a balloon-filled H2 atmosphere, the reaction suspension was stirred at RT for 2 h. The reaction was then quenched with CH2Cl2, filtered through a bed of celite and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Workup

  1. customThe vessel was then evacuated
  2. custompurged with H2
  3. customThe reaction was then quenched with CH2Cl2
  4. filtrationfiltered through a bed of celite
  5. concentrationthe filtrate concentrated in vacuo
  6. customPurification of the crude product
  7. customthus obtained by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-cb4c8964602d42a1a77523baf2db181e
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

Loading…