2-Chlorobenzaldehyde → HCID 23294852、化合物

HRID 1004319ノート

反応式

HRID 1004319 の反応式
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([CH2:7][N:8]2[CH:12]=[N:11][N:10]=[N:9]2)=[CH:5][CH:4]=1.C([Li])CCC.[Cl:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=[O:24]>O1CCCC1>[Cl:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]([C:12]1[N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:14][CH:13]=2)[N:9]=[N:10][N:11]=1)[OH:24]

参加物

5

反応物 3

HCID 69962-ChlorobenzaldehydeHCID 109978051-((4-methoxyphenyl)methyl)-1H-1,2,3,4-tetrazoleHCID 178418339Butyllithium

生成物 1

HCID 23294852HCID 23294852、化合物収率 12.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 1-(4-methoxybenzyl)tetrazole (6.12 g; Y. Satoh and N. Marcopulos, Tetrahedron Letters, 1995, 36, 1759-1762), and N,N,N'N'-tetramethylethylenediamine (10 ml) in dry tetrahydrofuran (10 ml) under nitrogen was cooled to -95° C. and treated dropwise with n-butyl lithium (2.5M solution in hexanes) over 15 minutes. The reaction mixture was left at -80° C. for 15 minutes when 2-chlorobenzaldehyde (4.53 g) was added dropwise over 10 minutes maintaining the reaction temperature at or below -80° C. The mixture was stirred at or below -80° C. for 30 minutes, allowed to warn to room temperature, quenched with ammonium chloride solution (50 ml) and the organic phase separated. The aqueous phase was extracted three times with ethyl acetate (50 ml), the combined organics dried over magnesium sulphate and evaporated. The residue was purified by flash chromatography on silica eluting initially with a mixture of ethyl acetate and pentane (1:1, v/v) then with a mixture of ethyl acetate and pentane (2:1, v/v). Fractions homogenous in the required product were combined and evaporated affording the title compound (1.33 g) as a white solid, m.p. 128-130° C. [Elemental analysis:- C,58.22; H,4.74; N,17.15%. Calculated:- C,58.1; H,4.57; N,16.94%].

後処理

  1. additionwas added dropwise over 10 minutes
  2. temperaturemaintaining the reaction temperature at or below -80° C
  3. customto warn to room temperature
  4. customquenched with ammonium chloride solution (50 ml)
  5. customthe organic phase separated
  6. extractionThe aqueous phase was extracted three times with ethyl acetate (50 ml)
  7. dry with materialthe combined organics dried over magnesium sulphate
  8. customevaporated
  9. customThe residue was purified by flash chromatography on silica eluting initially with a mixture of ethyl acetate and pentane (1:1
  10. additionv/v) then with a mixture of ethyl acetate and pentane (2:1
  11. customevaporated

出典と根拠

ORDレコード
ord-c493d0902a08429a8beb1a80d2037fd3
出典データセット
uspto-grants-2000_04
特許番号
US06048893

反応ノート

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