Dodecanoyl chloride → 4-(N-Dodecanoylaminomethyl)-2-triethylsilylfuran

HRID 1090884Notes

Reaction equation

HRID 1090884 reaction equation
[C:1](Cl)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[NH2:15][CH2:16][C:17]1[CH:18]=[C:19]([Si:22]([CH2:27][CH3:28])([CH2:25][CH3:26])[CH2:23][CH3:24])[O:20][CH:21]=1.C(N(CC)CC)C>O1CCCC1>[C:1]([NH:15][CH2:16][C:17]1[CH:18]=[C:19]([Si:22]([CH2:25][CH3:26])([CH2:27][CH3:28])[CH2:23][CH3:24])[O:20][CH:21]=1)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 8166Dodecanoyl chlorideHCID 8471TriethylamineHCID 150370494-Aminomethyl-2-triethylsilylfuran2×

Product 1

HCID 150370504-(N-Dodecanoylaminomethyl)-2-triethylsilylfuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dodecanoyl chloride (109 mg, 0.49 mmol) was added to a solution of 4-aminomethyl-2-triethylsilylfuran (Compound 2, 70 mg, 0.33 mmol) and triethylamine (69 microliter, 0.49 mmol) in tetrahydrofuran (3 ml) at room temperature. After stirring at room temperature overnight (ca. 15 hours), most of the solvent was evaporated and the residue was purified by chromatography on preparative silica thin layer plates (developed with 50% ethyl ether/hexane) to give the title amide as a colorless oil.

Workup

  1. custommost of the solvent was evaporated
  2. customthe residue was purified by chromatography on preparative silica thin layer plates (developed with 50% ethyl ether/hexane)

Sources & evidence

ORD record
ord-0e90276c0e494278a371468c9465a033
Source dataset
uspto-grants-1992_01
Patent number
US05082954

Reaction notes

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