Tetrahydrofuran → N-[2-t-Butyl-5-(2-cyclohexyl-1-hydroxyethyl)phenyl]-2-(9H-xanthen-9-yl)acetamide

HRID 977822노트

반응식

HRID 977822 반응식
O1CCCC1.[C:6]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[O:17])=[CH:12][C:11]=1[NH:18][C:19](=[O:35])[CH2:20][CH:21]1[C:34]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:28][C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)([CH3:9])([CH3:8])[CH3:7].[CH:36]1([CH2:42][Mg]Br)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>C(OCC)C>[C:6]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]([OH:17])[CH2:42][CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)=[CH:12][C:11]=1[NH:18][C:19](=[O:35])[CH2:20][CH:21]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=2[O:28][C:29]2[C:34]1=[CH:33][CH:32]=[CH:31][CH:30]=2)([CH3:9])([CH3:7])[CH3:8]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 19966116N-(2-t-butyl-5-formylphenyl)-2-(9H-xanthen-9-yl)acetamideHCID 178419664HCID 178419664, 화합물

생성물 1

HCID 19966142N-[2-t-Butyl-5-(2-cyclohexyl-1-hydroxyethyl)phenyl]-2-(9H-xanthen-9-yl)acetamide수율 76%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

8 ml of a tetrahydrofuran solution containing 100 mg (0.25 mmol) of N-(2-t-butyl-5-formylphenyl)-2-(9H-xanthen-9-yl)acetamide (prepared as described in Preparation 15) were cooled in an ice bath. 0.38 ml (0.38 mmol) of a 1M solution of cyclohexylmethylmagnesium bromide in diethyl ether was then added dropwise to the solution. The resulting mixture was stirred for 20 minutes at this temperature. It was then diluted with diethyl ether, and washed with dilute aqueous hydrochloric acid and then with water. The solvent was then removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 20 g of silica gel. Elution with mixtures of methylene chloride and ethyl acetate ranging from 7:1 to 2:1 by volume afforded 95 mg (yield 76%) of the title compound as a foam-like substance.

후처리

  1. temperaturewere cooled in an ice bath
  2. washwashed with dilute aqueous hydrochloric acid
  3. customThe solvent was then removed by distillation under reduced pressure
  4. washElution with mixtures of methylene chloride and ethyl acetate ranging from 7:1 to 2:1 by volume

출처 및 근거

ORD 기록
ord-42b32d5f4ec74e61b25112572277e2f3
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05614550

반응 노트

불러오는 중…