Ethyl vinyl ether → 2-Bromo-4-(1-ethoxy-ethoxy)-but-1-ene

HRID 1265982ノート

反応式

HRID 1265982 の反応式
[Br:1][C:2](=[CH2:6])[CH2:3][CH2:4][OH:5].[CH:7]([O:9][CH2:10][CH3:11])=[CH2:8]>C(OCC)C.C(N(CC)CC)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]([CH2:3][CH2:4][O:5][CH:7]([O:9][CH2:10][CH3:11])[CH3:8])=[CH2:6]

参加物

6

反応物 2

HCID 8023Ethyl vinyl etherHCID 5339753-Bromo-3-buten-1-ol

生成物 1

HCID 185482072-Bromo-4-(1-ethoxy-ethoxy)-but-1-ene収率 91.6%

試薬・触媒・溶媒 3

HCID 8471Triethylamine触媒HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 3283Diethyl Ether溶媒

実験手順

While cooling a solution of 10.38 g (0.0687 mol) of 3-bromo-3-buten-1-ol in 20 ml of diethyl ether with 50 mg (0.000263 mol) p-toluene sulfonic acid monohydrate in an ice water bath, 19 ml (0.199 mol) of ethyl vinyl ether was added slowly dropwise to maintain an internal temperature of <10° C. After 1 hour at 0° C., a few drops of triethylamine was added. The reaction mixture was poured onto water. The resulting mixture was transferred to a separatory funnel and the phases were separated. The isolated organic layer was washed with brine then dried over potassium carbonate and filtered. The solvent was removed from the filtrate in vacuo to yield 14.04 g of 2-bromo-4-(1-ethoxy-ethoxy)-but-1-ene as an oil.

後処理

  1. temperatureto maintain an internal temperature of <10° C
  2. additionThe reaction mixture was poured onto water
  3. customThe resulting mixture was transferred to a separatory funnel
  4. customthe phases were separated
  5. washThe isolated organic layer was washed with brine
  6. dry with materialthen dried over potassium carbonate
  7. filtrationfiltered
  8. customThe solvent was removed from the filtrate in vacuo

出典と根拠

ORDレコード
ord-76ebaf9507254ae199d91d59c0e642b1
出典データセット
uspto-grants-2003_04
特許番号
US06548448B2

反応ノート

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