Pyridine → 4-Dodecoyloxymethyl-2-trimethylsilylfuran

HRID 654918노트

반응식

HRID 654918 반응식
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([Si:8]([CH3:11])([CH3:10])[CH3:9])[O:6][CH:7]=1.N1C=CC=CC=1.[C:18](Cl)(=[O:30])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>O1CCCC1>[C:18]([O:1][CH2:2][C:3]1[CH:4]=[C:5]([Si:8]([CH3:11])([CH3:10])[CH3:9])[O:6][CH:7]=1)(=[O:30])[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 3

HCID 1049PyridineHCID 8166Dodecanoyl chlorideHCID 13333558(2-Trimethylsilyl-4-furyl)methanol

생성물 1

HCID 150370464-Dodecoyloxymethyl-2-trimethylsilylfuran

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 4-hydroxymethyl-2-trimethylsilylfuran (0.288 g., 1.70 mmol) and pyridine (0.214 g., 2.55 mmol) in 30 ml dry tetrahydrofuran at 0° was added lauroyl chloride (0.408 g., 1.86 mmol). This solution was allowed to warm to room temperature, stirred 30 minutes, and partitioned between ethyl ether and 5% sodium bicarbonate solution. The organic portion was washed with aqueous cupric sulfate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to a colorless oil. This material was purified by flash chromatography (silica, 5% ethyl ether/petroleum ether) to give the desired ester.

후처리

  1. custompartitioned between ethyl ether and 5% sodium bicarbonate solution
  2. washThe organic portion was washed with aqueous cupric sulfate solution, water, saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a colorless oil
  6. customThis material was purified by flash chromatography (silica, 5% ethyl ether/petroleum ether)

출처 및 근거

ORD 기록
ord-3101aeadfe724ac5a465f4eed5280e48
출처 데이터셋
uspto-grants-1992_07
특허 번호
US05134128

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