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

HRID 488231Notes

Reaction equation

HRID 488231 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 chromatography 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 chromatography 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-f8016cc81bfd41548b2e81d770fabd5f
Source dataset
uspto-grants-1994_03
Patent number
US05298633

Reaction notes

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