1-Bromododecane → HCID 85976847、化合物

HRID 1062946ノート

反応式

HRID 1062946 の反応式
[H-].[Na+].[CH3:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]Br.[CH2:16]([OH:29])[CH2:17][CH2:18][CH2:19][C:20]#[C:21][C:22]#[C:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28]>CN(C=O)C>[OH:29][CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[C:21][C:22]#[C:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH3:3]

参加物

5

反応物 3

HCID 89191-BromododecaneHCID 24758Sodium hydrideHCID 5608785,7-Dodecadiyne-1,12-diol

生成物 1

HCID 85976847HCID 85976847、化合物収率 33.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In a glass reaction vessel, a suspension of 120 milligrams of sodium hydride was prepared in 10 milliliters dry DMF and 972 milligrams of 5,7-dodecadiyn-1,12-diol (HO(CH2)4C≡C—C≡C(CH2)4OH), was added. After stirring for 5 minutes 1.31 grams of CH3(CH2)11Br was added and the resulting mixture was stirred for 15 hours. The mixture was then quenched by addition of saturated NH4Cl solution and diluted with 100 milliliters of diethyl ether. The organic layer was separated and washed 3 times with brine, dried over MgSO4, filtered and the solvent was removed to yield a yellow oil. The oil was purified over silica gel (25%-35% by volume of ethyl acetate in hexanes gradient) to yield 606 milligrams of HO(CH2)4C≡C—C≡C(CH2)4O(CH2)11CH3 as a white solid.

後処理

  1. customIn a glass reaction vessel
  2. additionwas added
  3. customThe mixture was then quenched by addition of saturated NH4Cl solution
  4. additiondiluted with 100 milliliters of diethyl ether
  5. customThe organic layer was separated
  6. washwashed 3 times with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvent was removed
  10. customto yield a yellow oil
  11. customThe oil was purified over silica gel (25%-35% by volume of ethyl acetate in hexanes gradient)

出典と根拠

ORDレコード
ord-8771c6f5cc28409e9ee473e669fed5dd
出典データセット
uspto-grants-2005_11
特許番号
US06963007B2

反応ノート

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