Triphenylphosphine → Triphenylundecylphosphonium bromide

HRID 465402

반응식

HRID 465402 반응식
[CH2:1]([Br:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C(C)=CC=CC=1>[Br-:12].[CH2:1]([P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

참가 물질

4

반응물 2

HCID 11776TriphenylphosphineHCID 127441-Bromoundecane

생성물 1

HCID 3085198Triphenylundecylphosphonium bromide수율 64.7%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

A mixture of 14.1 g (60 mmol) of undecyl bromide and 15.7 g (60 mmol) of triphenylphosphine was refluxed in xylene for 15 hours, and the xylene was evaporated off. The mixture was added with ether and the supernatant was removed by decantation. This procedure was repeated thrice to obtain 19.3 g of undecyltriphenylphosphonium bromide. The bromide was dissolved in 200 ml of tetrahydrofuran and 20 ml (32 mmol) of a hexane solution (1.6 molar concentration) of 15% n-butyl lithium was added dropwise thereto under stirring and cooling with ice. After 10-minute stirring, a solution of 2.17 g (13 mmol) of (2-methoxycarbonylpyrrole)-4-acetaldehyde obtained in Synthesis Example 12 in 6 ml of tetrahydrofuran was added dropwise to the mixture under cooling with ice, and the mixture was allowed to react for 30 minutes. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was collected, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The residue obtained by evaporation was purified by a silica-gel column chromatography (eluent:ethyl acetate/hexane=1/10) to obtain 3.41 g of oil methyl 4-(2-tridecenyl)pyrrole-2-carboxylate. The yield was 86%.

후처리

  1. customthe xylene was evaporated off
  2. additionThe mixture was added with ether
  3. customthe supernatant was removed by decantation

출처 및 근거

ORD 기록
ord-0f9058de106048268c1e4a1f3efd76e6
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05153217

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