(E)-1-(2-Trimethylsilyl-4-furyl)-2-carbomethoxy-tridec-1-ene → 4-(2-Carbomethoxytridecyl)-2-trimethylsilylfuran

HRID 345886Notes

Reaction equation

HRID 345886 reaction equation
[CH3:1][Si:2]([CH3:26])([CH3:25])[C:3]1[O:4][CH:5]=[C:6](/[CH:8]=[C:9](/[C:21]([O:23][CH3:24])=[O:22])\[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:7]=1>C(OCC)(=O)C.[Rh]>[C:21]([CH:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:8][C:6]1[CH:7]=[C:3]([Si:2]([CH3:26])([CH3:1])[CH3:25])[O:4][CH:5]=1)([O:23][CH3:24])=[O:22]

Participants

4

Reactant 1

HCID 19991610(E)-1-(2-Trimethylsilyl-4-furyl)-2-carbomethoxy-tridec-1-ene

Product 1

HCID 199916134-(2-Carbomethoxytridecyl)-2-trimethylsilylfuran

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (E)-1-(2-trimethylsilyl-4-furyl)-2-carbomethoxytridec-1-ene (133 mg, 0.35 mmole) in ethyl acetate (20 ml) was hydrogenated over 5% rhodium on alumina (ca 10 mg) at room temperature for 3 days. The mixture was filtered through celite and the filtrate on evaporation gave an oil which was purified by preparative TLC (20×20 cm, 1000μ silica plate; developed with 10% ethyl ether/hexane). The title ester was obtained as a colorless oil.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthe filtrate on evaporation
  3. customgave an oil which
  4. customwas purified by preparative TLC (20×20 cm, 1000μ silica plate; developed with 10% ethyl ether/hexane)

Sources & evidence

ORD record
ord-3e1212e6f36541319593b339d21b5c82
Source dataset
uspto-grants-1991_10
Patent number
US05059611

Reaction notes

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