1,10-Dibromodecane → 1-Bromohexadec-1-yne

HRID 1719648ノート

反応式

HRID 1719648 の反応式
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][Br:12].[C:13]([Li])#[C:14][CH2:15][CH2:16][CH2:17][CH3:18]>C1COCC1.CN(P(N(C)C)N(C)C)C>[C:11]([Br:12])#[C:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

参加物

5

反応物 2

HCID 2214831,10-DibromodecaneHCID 178506798HCID 178506798、化合物

生成物 1

HCID 198481531-Bromohexadec-1-yne収率 34.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 15355Hexamethylphosphorous triamide溶媒

実験手順

A 3 liter, 2-necked round bottom flask was equipped with a magnetic stir bar, an inlet valve and a septum. After being purged with an argon atmosphere, the flask was charged with 615 g (2.1 mol) of 1,10-dibromodecane in 350 mL of THF and 125 mL of hexamethylphosphorus triamide. A solution containing about 1 mol of hexynyllithium, prepared as described above, was then added to the solution of dibromide via the septum. The reaction mixture was allowed to stir overnight, then quenched by pouring over about 1 L of water. The reaction mixture was diluted with about 500 mL of hexane, phases separated and the organic layer washed twice with 500 mL aliquots of water. The organic layer was then dried over MgSO4, filtered, solvent stripped on the rotary evaporator, then vacuum distilled through a 2 foot column packed with 1/4" glass helices. About 104 g (35 mol % yield) of hexadecynyl bromide was obtained with a boiling point of 135° C. @ 0.3 mm Hg.

後処理

  1. customA 3 liter, 2-necked round bottom flask was equipped with a magnetic stir bar, an inlet valve
  2. customAfter being purged with an argon atmosphere
  3. customprepared
  4. customquenched
  5. additionby pouring over about 1 L of water
  6. additionThe reaction mixture was diluted with about 500 mL of hexane, phases
  7. customseparated
  8. washthe organic layer washed twice with 500 mL aliquots of water
  9. dry with materialThe organic layer was then dried over MgSO4
  10. filtrationfiltered
  11. customsolvent stripped on the rotary evaporator
  12. distillationvacuum distilled through a 2 foot column

出典と根拠

ORDレコード
ord-f64d56807b324c4a874c48387e8f3000
出典データセット
uspto-grants-1985_09
特許番号
US04540826

反応ノート

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