Trichloroacetic Acid → Methyl 5-[cyanohydroxy(4-methylphenyl)methyl]-1-methylpyrrole-2-acetate

HRID 848040

反応式

HRID 848040 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([C:8]#[N:9])=[O:7])=[CH:4][CH:3]=1.[CH3:12][N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][C:19]([O:21][CH3:22])=[O:20].ClC(Cl)(Cl)C(O)=O>CCOCC>[C:8]([C:6]([OH:7])([C:5]1[CH:10]=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=1)[C:17]1[N:13]([CH3:12])[C:14]([CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:16]=1)#[N:9]

参加物

5

反応物 3

HCID 6421Trichloroacetic AcidHCID 103992Methyl 1-methylpyrrol-2-acetateHCID 641326Oxo-P-tolyl-acetonitrile

生成物 1

HCID 12940095Methyl 5-[cyanohydroxy(4-methylphenyl)methyl]-1-methylpyrrole-2-acetate収率 16%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A solution of 1.45 g (0.01 mole) of 4-methylbenzoylcyanide, 1.5 g (0.01 mole) of methyl 1-methylpyrrole-2-acetate and 40 mg (0.25 mmoles) of trichloroacetic acid in 4 ml of ether was stirred at 25° under nitrogen for 21 days. The precipitated solid was collected by filtration and washed with cold ether, than hexane. The combined filtrates were evaporated in vacuo. A second crop of crystals was taken from hexane. After recrystallization from toluene:hexane was obtained, 0.46 g (16 percent yield) of methyl 5-[cyanohydroxy(4-methylphenyl)-methyl]-1-methylpyrrole-2-acetate mp 117°-118°. H1NMR CDCl3 2.35 (s, 3 H); 3.35 (s, 3 H); 3.55 (s, 2H); 3.65 (s, 3 H); 5.90 (d, 1 H); 6.05 (d, 1H); 7.15 (d, 2H); 7.35 (d, 2H). MS m/e 281, 280, 266, 212 IRnujol 3425, 1700 cm-1.

後処理

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with cold ether, than hexane
  3. customThe combined filtrates were evaporated in vacuo
  4. customAfter recrystallization from toluene
  5. customhexane was obtained

出典と根拠

ORDレコード
ord-b2dca4c3d0d54749a8892380e6b6ad9b
出典データセット
uspto-grants-1981_10
特許番号
US04294760

関連ノート

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