Diethyl Ether → 7-Methoxyhept-1-yne

HRID 1511871ノート

反応式

HRID 1511871 の反応式
[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]

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 6328Methyl iodide2 回HCID 24758Sodium hydride3 回HCID 110078496-Heptyn-1-ol

生成物 1

HCID 575547897-Methoxyhept-1-yne収率 61.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

  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.)

出典と根拠

ORDレコード
ord-2770c457b06c4249af250c83c3e317f7
出典データセット
uspto-grants-2012_07
特許番号
US08217027B2

反応ノート

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