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

HRID 618302ノート

反応式

HRID 618302 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 154095301-Methoxy-7-(4-pentenyloxy)heptane収率 16.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-eea7e804209c47989df5fedc9e16d2b9
出典データセット
uspto-grants-1999_09
特許番号
US05952377

反応ノート

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