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

HRID 1090911

반응식

HRID 1090911 반응식
[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]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 150370354-Hydroxymethyl-2-triethylsilylfuran2회

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aaa7c4a90201477589f1079eb55d4670
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05082954

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