Water → 1-Methoxy-7-(4-pentenyloxy)heptane

HRID 583211노트

반응식

HRID 583211 반응식
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12].Br[CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18].O>O1CCCC1>[CH3:3][O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH2:18][CH2:17][CH2:16][CH:15]=[CH2:14]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 707041-Pentene, 5-bromo-HCID 154095297-Methoxy-1-heptanol

생성물 1

HCID 154095301-Methoxy-7-(4-pentenyloxy)heptane수율 16.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Sodium hydride (665 mg, 17 mmol, washed three times with hexane) was treated with the title product of Example 3 (2.0 g, 14 mmol) in 90 mL of tetrahydrofuran at reflux for one hour. A solution of 5-bromopentene (2.0 g, 14 mmol) in 50 mL of tetrahydrofuran was added dropwise and refluxing continued for 20 hours. After cooling to room temperature, 50 mL of water was added, the layers separated and the aqueous phase was extracted with two portions of ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Chromatography of the crude residue on silica gel using 50-50 ethyl acetate-heptane as eluant gave the title compound (485 mg) as a yellow oil and the structure verified by NMR.

후처리

  1. temperatureat reflux for one hour
  2. temperaturerefluxing
  3. customthe layers separated
  4. extractionthe aqueous phase was extracted with two portions of ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1bc049a6894848ad887e43a1e22c2824
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05929110

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