Propyltriphenylphosphonium bromide → 1-(3-Chloro-4,5-dipropargyloxyphenyl)butene

HRID 1608130ノート

反応式

HRID 1608130 の反応式
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH3:4].C([Li])CCC.[Cl:29][C:30]1[CH:31]=[C:32]([CH:35]=[C:36]([O:42][CH2:43][C:44]#[CH:45])[C:37]=1[O:38][CH2:39][C:40]#[CH:41])[CH:33]=O>C(OCC)C>[Cl:29][C:30]1[CH:31]=[C:32]([CH:33]=[CH:2][CH2:3][CH3:4])[CH:35]=[C:36]([O:42][CH2:43][C:44]#[CH:45])[C:37]=1[O:38][CH2:39][C:40]#[CH:41]

参加物

5

反応物 3

HCID 80374Propyltriphenylphosphonium bromideHCID 141303053-Chloro-4,5-dipropargyloxybenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 538238081-(3-Chloro-4,5-dipropargyloxyphenyl)butene収率 81.5%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

n-Propyltriphenylphosphonium bromide (4.66 g) was dissolved in dry diethyl ether (50 ml), and n-butyl lithium (7.6 ml; 1.6N) was added thereto at 0° C. under nitrogen stream, followed by stirring at room temperature for 3 hours. A solution of 3-chloro-4,5-dipropargyloxybenzaldehyde (3.0 g) in dry diethyl ether (50 ml) was dropwise added to the resultant mixture, which was stirred at room temperature overnight, poured into ice-water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using toluene as an eluent to give 1-(3-chloro-4,5-dipropargyloxyphenyl)butene (2.7 g). nD25.0 1.5602.

後処理

  1. customat 0° C.
  2. stirringwas stirred at room temperature overnight
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-80fc832a51044d8c82e3a9e17819d6f2
出典データセット
uspto-grants-1989_09
特許番号
US04870064

反応ノート

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