N,N,N',N'-Tetramethylethylenediamine → 2,6,10,15,19,23-Hexamethyltetracosa-11,13-diyne-10,15-diol

HRID 596562ノート

反応式

HRID 596562 の反応式
[CH3:1][C:2]([OH:16])([CH2:5][CH2:6][CH2:7][CH:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[C:3]#[CH:4].CN(C)[CH2:19][CH2:20]N(C)C>N1C=CC=CC=1>[CH3:13][CH:12]([CH2:11][CH2:10][CH2:9][CH:19]([CH3:20])[CH2:7][CH2:6][CH2:5][C:2]([CH3:1])([OH:16])[C:3]#[C:4][C:4]#[C:3][C:2]([CH3:1])([OH:16])[CH2:5][CH2:6][CH2:7][CH:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:13])[CH3:14])[CH3:14]

参加物

4

反応物 2

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 1026523,7,11-Trimethyldodecyn-3-ol

生成物 1

HCID 214273422,6,10,15,19,23-Hexamethyltetracosa-11,13-diyne-10,15-diol収率 81.8%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

In a 1-l three-necked and round-bottomed flask 10.5 g of 3,7,11-trimethyldodeca-1-yne-3-ol, 5.0 g of cuprous chloride, 12.0 g of tetramethylethylenediamine and 675 ml of pyridine were placed and the mixture was subjected to oxydative coupling reaction at 50° ~ 55° C for 6 hours under an oxygen atmosphere. After completion of the reaction, there remained no unreacted starting alcohol. The pyridine was distilled off the reaction system and 300 ml of benzene and 200 ml of water were added to the residue and decanted. The organic layer was washed with 3N--H2SO4 and water, and dried. The benzene was distilled off to afford 8.55 g of 2,6,10,15,19,23-hexamethyltetracosa-11,13-diyne-10,15-diol. A 5.0 g portion of this product was dissolved in 10 ml of n-hexane and 0.25 g of 3 % palladium on active carbon was added thereto. The mixture was subjected to hydrogenation at a temperature of 60° C of under a hydrogen pressure of 3 ~ 5 kg/cm2 to give 4.6 g of the product consisting of the compounds (V) and (VI) in the ratio of 95.0 : 5.0 % respectively.

後処理

  1. customthe mixture was subjected to oxydative coupling reaction at 50° ~ 55° C for 6 hours under an oxygen atmosphere
  2. customAfter completion of the reaction, there
  3. distillationThe pyridine was distilled off the reaction system and 300 ml of benzene and 200 ml of water
  4. additionwere added to the residue
  5. customdecanted
  6. washThe organic layer was washed with 3N
  7. dry with materialH2SO4 and water, and dried
  8. distillationThe benzene was distilled off

出典と根拠

ORDレコード
ord-35f25b637cbd4a0fb6c84688f60f58a6
出典データセット
uspto-grants-1977_03
特許番号
US04011277

反応ノート

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