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

HRID 129344
ノート
印刷プレビュー

反応式

HRID 129344 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-b3178c436b744eec97f807fde774d867
出典データセット
uspto-grants-1995_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
USRE035096

反応ノート

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