HCID 70048572, compound → HCID 18949912, compound

HRID 727956Notes

Reaction equation

HRID 727956 reaction equation
[CH:1](/[C:14]1[CH:15]=[C:16]([Si:19]([CH3:22])([CH3:21])[CH3:20])[O:17][CH:18]=1)=[CH:2]/[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>C(OCC)C.[Pd]>[CH2:1]([C:14]1[CH:15]=[C:16]([Si:19]([CH3:22])([CH3:21])[CH3:20])[O:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 1

HCID 70048572HCID 70048572, compound

Product 1

HCID 18949912HCID 18949912, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of (E), (Z)-4-(1-tridecenyl)-2-trimethylsilylfuran (2.0 g, 6.25 mmol) and 10% palladium or carbon (20 mg) in ethyl ether (10 ml) was hydrogenated at room temperature for 7 h. The mixture was filtered through celite and the filtrate upon evaporation gave essentially pure 4-tridecyl-2-trimethylsilylfuran. The silylfuran was redissolved in tetrahydrofuran (8 ml) and was exposed to singlet oxygen, in the presence of Rose Bengal (5 mg), for 2 h at 0°. The residue, after solvent removal, was purified by a silica column using 60% ethyl ether/hexane to give the titled furanone.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe filtrate upon evaporation

Sources & evidence

ORD record
ord-9f49eb97af294c6d95e1d259d08346cd
Source dataset
uspto-grants-1991_09
Patent number
US05045564

Reaction notes

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