1-(triphenylmethyl)-1H-imidazole-4-carbaldehyde → HCID 54381600, 화합물

HRID 1756953

반응식

HRID 1756953 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 54381600HCID 54381600, 화합물수율 64%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b05c7116fe4842f4b46bea5f2dd6778f
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05441975

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