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Tetrahydrofuran → Methyl 4-(1-cis tridecenyl)pyrrole-2-carboxylate

HRID 1090747
ノート
印刷プレビュー

反応式

HRID 1090747 の反応式
C([Li])CCC.O1CCCC1.[Br-].[CH2:12]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[CH:43]([C:45]1[CH:46]=[C:47]([C:50]([O:52][CH3:53])=[O:51])[NH:48][CH:49]=1)=O>CCCCCC.O>[CH:43](/[C:45]1[CH:46]=[C:47]([C:50]([O:52][CH3:53])=[O:51])[NH:48][CH:49]=1)=[CH:23]/[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 84955Dodecyltriphenylphosphonium bromideHCID 640310methyl 4-formyl-1H-pyrrole-2-carboxylateHCID 178418339Butyllithium

生成物 1

HCID 15023334Methyl 4-(1-cis tridecenyl)pyrrole-2-carboxylate収率 65%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 8058Hexane溶媒

実験手順

A ca. 15% solution (18.5 ml) of n-butyllithium in hexane was added dropwise at -50° C. to a tetrahydrofuran suspension (95 ml) of 16.0 g (31.4 mmol) of dodecyltriphenylphosphonium bromide described in Chemistry and Industry (London) p. 1086, 1958. The temperature was raised to room temperature and the mixture was stirred for 30 minutes. The temperature was again lowered to -50° C. To the mixture was added dropwise a tetrahydrofuran solution (50 ml) of 2.4 g (15.7 mmol) of methyl 4-formylpyrrole-2-carboxylate described in Bulletin de la Societe Chimique de France, p. 283, 1972. The mixture was stirred for 1 hour, diluted with water, extracted with ethyl acetate, washed with an aqueous saturated solution of sodium chloride and dried over anhydrous magnesium sulfate. After removing the solvent under reduced pressure, the residue was purified by subjecting it to column chromatography over silica gel (eluent: ethyl acetate/hexane=1/7) to obtain 3.11 g (65% yield) of methyl 4-(1-cis-tridecenyl)pyrrole-2-carboxylate, m.p. 51°-52° C.

後処理

  1. customwas again lowered to -50° C
  2. stirringThe mixture was stirred for 1 hour
  3. extractionextracted with ethyl acetate
  4. washwashed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removing the solvent under reduced pressure
  7. customthe residue was purified

出典と根拠

ORDレコード
ord-cfdccdfada6946fe9f6ecb05d73fadd9
出典データセット
uspto-grants-1992_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05082856

反応ノート

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