Tetrahydrofuran → 4-Dodecanoxy-2-triethylsilylfuran

HRID 488203

반응식

HRID 488203 반응식
OC[C:3]1[CH:4]=[C:5]([Si:8]([CH2:13][CH3:14])([CH2:11][CH3:12])[CH2:9][CH3:10])[O:6][CH:7]=1.[H-].[K+].I[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[O:30]1CCCC1>>[CH2:18]([O:30][C:3]1[CH:4]=[C:5]([Si:8]([CH2:9][CH3:10])([CH2:11][CH3:12])[CH2:13][CH3:14])[O:6][CH:7]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

참가 물질

5

반응물 4

HCID 8028Tetrahydrofuran2회HCID 202821-IodododecaneHCID 82127Potassium hydride2회HCID 150370354-Hydroxymethyl-2-triethylsilylfuran2회

생성물 1

HCID 190198574-Dodecanoxy-2-triethylsilylfuran

실험 절차

A solution of 4-hydroxymethyl-2-triethylsilylfuran (Compound 1, 160 mg, 0.75 mmol) in tetrahydrofuran (0.5 ml) was added to a suspension of potassium hydride (33 mg, 0.83 mmol) in tetrahydrofuran (1 ml) at room temperature. When all the potassium hydride disappeared, 1-iodododecane (0.37 ml, 1.5 mmol) was added. Stirring was continued for 4 days at room temperature. The reaction mixture was quenched with water. Extraction (ethyl ether) 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 0.65 on evaporation gave the titled ether as a pale yellow oil.

후처리

  1. customThe reaction mixture was quenched with water
  2. extractionExtraction (ethyl ether) 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 0.65 on evaporation
  7. customgave the titled ether as a pale yellow oil

출처 및 근거

ORD 기록
ord-413aef5246c04bbdab4f6f30a2fe0bdb
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05298633

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