Water → 4-Tert-butyl-2-(2-oxo-2-phenylethyl)-cyclohexanone

HRID 1504994

반응식

HRID 1504994 반응식
[C:1]([CH:5]1[CH2:10][CH2:9][C:8](N2CCCC2)=[CH:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19].[OH2:26]>CN(C=O)C>[C:1]([CH:5]1[CH2:6][CH2:7][C:8](=[O:26])[CH:9]([CH2:17][C:18](=[O:19])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

5

반응물 3

HCID 962WaterHCID 6259Phenacyl bromideHCID 1072321-[4-(Tert-butyl)-1-cyclohexen-1-YL]pyrrolidine

생성물 1

HCID 122703414-Tert-butyl-2-(2-oxo-2-phenylethyl)-cyclohexanone

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a 250-mL round-bottomed flask containing 3.3 mL of 1-(4-tert-butylcyclohex-1-enyl) pyrrolidine was added 100 mL anhydrous DMF, under nitrogen. The flask was fitted with an addition funnel containing 2-bromoacetophenone (4.12 gm) in 35 mL anhydrous DMF, which was dripped into the enamine solution over 60 min. This solution was stirred at ambient temperature for 10 hr, then 90 mL water was added to the solution and it was stirred for another 11 hr, under nitrogen. The solution was then extracted twice with ethyl acetate and water, the organic layers combined and further washed with water (3×), dried over sodium sulfate, filtered and rotovapped down to give a yellow oil. The oil was purified by MPLC using 10% ethyl acetate/hexanes.

후처리

  1. customThe flask was fitted with an addition funnel
  2. stirringwas stirred for another 11 hr, under nitrogen
  3. extractionThe solution was then extracted twice with ethyl acetate and water
  4. washfurther washed with water (3×)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customto give a yellow oil
  8. customThe oil was purified by MPLC

출처 및 근거

ORD 기록
ord-aef2f0db77e943c6a1fdacc4326457ab
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216966B2

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