4-(Bromomethyl)benzonitrile → HCID 54160280, 화합물

HRID 443229노트

반응식

HRID 443229 반응식
[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[N:6]=[CH:7][N:8]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[C:40]([C:42]1[CH:49]=[CH:48][C:45]([CH2:46]Br)=[CH:44][CH:43]=1)#[N:41]>C1COCC1>[CH3:1][O:2][C:3](=[O:29])[CH:4]([C:5]1[N:6]=[CH:7][N:8]([C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=1)[CH2:46][C:45]1[CH:48]=[CH:49][C:42]([C:40]#[N:41])=[CH:43][CH:44]=1

참가 물질

5

반응물 3

HCID 869964-(Bromomethyl)benzonitrileHCID 2733832Lithium HexamethyldisilazideHCID 105239671-(triphenylmethyl)-1H-Imidazole-4-acetic acid methyl ester

생성물 1

HCID 54160280HCID 54160280, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

A solution of 1-(triphenylmethyl)-1H-imidazol-4-ylacetic acid methyl ester (977 mg, 2.55 mmol) in THF (25 ml) was cooled to -78° C. Lithium hexamethyldisilazide (2.68 ml, 2.68 mmol) was added dropwise and the reaction stirred 30 min at -78° C. 4-Cyanobenzyl bromide (500.7 mg, 2.68 mmol) was added and the reaction stirred a furthur 4 hrs at -78° C. and then at -20° C. for 12 hr. The reaction was quenched with water (10 ml) and saturated NaHCO3 solutuon (10 ml) and extracted with EtOAc. The organic extracts were dried (MgSO4) and the solvent evaporated in vacuo. Chromatography of the residue (SiO2, 3% MeOH in CH2Cl2) afforded the product.

후처리

  1. stirringthe reaction stirred a furthur 4 hrs at -78° C.
  2. waitat -20° C. for 12 hr
  3. customThe reaction was quenched with water (10 ml) and saturated NaHCO3 solutuon (10 ml)
  4. extractionextracted with EtOAc
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. customthe solvent evaporated in vacuo
  7. customChromatography of the residue (SiO2, 3% MeOH in CH2Cl2) afforded the product

출처 및 근거

ORD 기록
ord-0c9b1c59d4674956bfcd606d104b7072
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891889

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