1-(triphenylmethyl)-1H-imidazole-4-carbaldehyde → HCID 54381600、化合物

HRID 1756953

反応式

HRID 1756953 の反応式
[Li]CCCC.[Br-].[CH2:7]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[C:37]1([C:43]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[N:44]2[CH:48]=[C:47]([CH:49]=O)[N:46]=[CH:45]2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C1COCC1>[CH:49]([C:47]1[N:46]=[CH:45][N:44]([C:43]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:48]=1)=[CH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH3:7]

参加物

5

反応物 3

HCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 3085198Triphenylundecylphosphonium bromideHCID 178418339Butyllithium

生成物 1

HCID 54381600HCID 54381600、化合物収率 64%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of n-BuLi (4.1 mL, 6.5 mmol, 1.6M in hexanes) was added dropwise to a suspension of n-undecyl-triphenylphosphoniumbromide (3.09 g, 6.2 mmol, obtained from triphenylphosphine and undecylbromide) in 100 mL THF at -78° C. under an atmosphere of N2. The resulting orange solution was stirred for 45 minutes before a solution of 1-(triphenylmethyl)-4-imidazolecarboxaldehyde (2.0 g, 5.9 mmol, Ref: Kelly JL, Miller CA, and McLean EW, J. Med. Chem. 1977;20:721) in 75 mL THF was added dropwise. Warmed to room temperature and stirred for 16 hours. Quenched by adding 50 mL saturated NH4Cl solution and concentrating in vacuo. The residue was partitioned between water and dichloromethane. The organic layer was dried over MgSO4, filtered, and concentrated to give a yellow oil. Chromatography (10% EtOAc/hexanes on silica) gave the title compound (1.8 g, 64% ) as a clear oil.

後処理

  1. customQuenched
  2. additionby adding 50 mL saturated NH4Cl solution
  3. concentrationconcentrating in vacuo
  4. customThe residue was partitioned between water and dichloromethane
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow oil

出典と根拠

ORDレコード
ord-b05c7116fe4842f4b46bea5f2dd6778f
出典データセット
uspto-grants-1995_08
特許番号
US05441975

関連ノート

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