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

HRID 1608130노트

반응식

HRID 1608130 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-80fc832a51044d8c82e3a9e17819d6f2
출처 데이터셋
uspto-grants-1989_09
특허 번호
US04870064

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