Diethyl Ether → 7-Methoxyhept-1-yne

HRID 1511871노트

반응식

HRID 1511871 반응식
[H-].[Na+].CI.[CH2:5]([OH:12])[CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[CH:11].[CH3:13]COCC>CN(C=O)C.O>[CH3:13][O:12][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[CH:11]

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 6328Methyl iodide2회HCID 24758Sodium hydride3회HCID 110078496-Heptyn-1-ol

생성물 1

HCID 575547897-Methoxyhept-1-yne수율 61.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

To a slurry of sodium hydride (7.86 g, 197 mmol) in DMF (100 mL) was added methyl iodide (12.29 mL, 197 mmol) followed by a solution of hept-6-yn-1-ol (24.5 g, 197 mmol) in DMF (50 mL). Following the addition the reaction was monitored by TLC. After 2 h additional methyl iodide (6 mL, 50 mmol) was added followed by sodium hydride (1 g, 25 mmol) portions. At 1 h intervals additional sodium hydride (1 g, 25 mmol) portions was added until no alcohol remained as indicated by TLC. Et2O (50 mL) and water (100 mL) was added to the reaction mixture and the layers were separated. The organic layer was washed with brine, dried using Na2SO4, filtered and distilled (145-155° C.) to provide 7-methoxyhept-1-yne (18 g, 121 mmol, 61.7% yield) as a colorless oil.

후처리

  1. additionthe addition the reaction
  2. customthe layers were separated
  3. washThe organic layer was washed with brine
  4. customdried
  5. filtrationfiltered
  6. distillationdistilled (145-155° C.)

출처 및 근거

ORD 기록
ord-2770c457b06c4249af250c83c3e317f7
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217027B2

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