Triethylamine → Bis-[(2-triethylsilyl-4-furyl)methyl]oxalate

HRID 1109891Notes

Reaction equation

HRID 1109891 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[OH:7][CH2:8][C:9]1[CH:10]=[C:11]([Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16])[O:12][CH:13]=1.C(N([CH2:26][CH3:27])CC)C>ClCCl>[CH2:15]([Si:14]([CH2:17][CH3:18])([CH2:19][CH3:20])[C:11]1[O:12][CH:13]=[C:9]([CH2:8][O:7][C:1](=[O:5])[C:2]([O:7][CH2:8][C:9]2[CH:10]=[C:11]([Si:14]([CH2:26][CH3:27])([CH2:17][CH3:18])[CH2:15][CH3:16])[O:12][CH:13]=2)=[O:3])[CH:10]=1)[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 150370354-Hydroxymethyl-2-triethylsilylfuran2×

Product 1

HCID 15037121Bis-[(2-triethylsilyl-4-furyl)methyl]oxalate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.59 ml, 6.79 mmol) was added dropwise to a solution of 4-hydroxymethyl-2-triethylsilylfuran (Compound 1, 1.2 g, 5.66 mmol) and triethylamine (0.95 ml, 6.79 mmol) in dichloromethane (10 ml) at 0°. After 10 minutes, the reaction mixture was quenched with ice. Extraction (dichloromethane) and evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by flash chromotograhy on silica using 5% ethyl ether/hexane. Fractions with Rf of about 0.17 gave, after evaporation the title oxalate ester as a colorless oil.

Workup

  1. customthe reaction mixture was quenched with ice
  2. extractionExtraction (dichloromethane) and evaporation of the
  3. dry with materialdried (magnesium sulfate)
  4. customextracts gave an oil, which
  5. customwas purified by flash chromotograhy on silica using 5% ethyl ether/hexane
  6. customFractions with Rf of about 0.17 gave
  7. customafter evaporation the title oxalate ester as a colorless oil

Sources & evidence

ORD record
ord-9b63b808f0ca44ccbdccd41d684fe43f
Source dataset
uspto-grants-1994_06
Patent number
US05322953

Reaction notes

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