Ammonia → 2,5-Dihydro-2,5-dimethoxy-2-(8,8,8-trimethoxy-3-octynyl)furan

HRID 1032504ノート

反応式

HRID 1032504 の反応式
[NH2-].[Li+].N.[CH3:4][O:5][C:6]1([CH2:13][CH2:14][C:15]#[CH:16])[CH:10]=[CH:9][CH:8]([O:11][CH3:12])[O:7]1.Br[CH2:18][CH2:19][CH2:20][C:21]([O:26][CH3:27])([O:24][CH3:25])[O:22][CH3:23]>O1CCCC1>[CH3:4][O:5][C:6]1([CH2:13][CH2:14][C:15]#[C:16][CH2:18][CH2:19][CH2:20][C:21]([O:26][CH3:27])([O:24][CH3:25])[O:22][CH3:23])[CH:10]=[CH:9][CH:8]([O:11][CH3:12])[O:7]1

参加物

6

反応物 4

HCID 222Ammonia2 回HCID 24532Lithium amideHCID 5187924Trimethyl 4-bromoorthobutyrateHCID 147744262,5-Dihydro-2,5-dimethoxy-2-(3-butynyl)furan

生成物 1

HCID 221661452,5-Dihydro-2,5-dimethoxy-2-(8,8,8-trimethoxy-3-octynyl)furan収率 108.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred mixture of 0.51 g of lithium amide and ml of liquid ammonia was added dropwise a solution of 3.64 g of 2,5-dihydro-2,5-dimethoxy-2-(3-butynyl)furan in 2.5 ml of tetrahydrofuran during 5 minutes. The mixture was stirred under reflux for 30 minutes and then treated dropwise with a solution of 5.0 g of 1-bromo-4,4,4-trimethoxybutane (U.S. Pat. No. 3,864,387) in 5 ml of tetrahydrofuran during 5 minutes. This solution was stirred under reflux for one hour, the ammonia allowed to evaporate during one hour and the resulting solution stirred at 20° C. for 10 minutes. This solution was partitioned with ether and brine. The organic layer was dried, treated with 2 drops of pyridine, and then concentrated, giving 7.1 g of the desired compound as a light amber oil; PMR δ 5.9 (2H, m, vinyl hydrogens).

後処理

  1. temperatureunder reflux for 30 minutes
  2. stirringThis solution was stirred
  3. temperatureunder reflux for one hour
  4. customto evaporate during one hour
  5. stirringthe resulting solution stirred at 20° C. for 10 minutes
  6. customThis solution was partitioned with ether and brine
  7. customThe organic layer was dried
  8. additiontreated with 2 drops of pyridine
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-ade4828b740c429e9484a8d1b2ed028f
出典データセット
uspto-grants-1990_09
特許番号
US04958037

反応ノート

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