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Dimethylformamide → Tert-butyl {4-[2-(benzyloxy)-2-oxoethyl]phenoxy}acetate

HRID 530929
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HRID 530929 반응식
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].CN(C)C=O.[OH:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])=[CH:24][CH:23]=1>O>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][C:25]1[CH:24]=[CH:23][C:22]([O:21][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:27][CH:26]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1
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참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 11107524Benzyl 2-(4-hydroxyphenyl)acetate

생성물 1

HCID 68357704Tert-butyl {4-[2-(benzyloxy)-2-oxoethyl]phenoxy}acetate수율 98.3%

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

Potassium carbonate (1.38 g) and tert-butyl bromoacetate (1.07 g) were added to a dehydrated N,N-dimethylformamide (17 mL) solution of benzyl (4-hydroxyphenyl)acetate (1.21 g) at room temperature, followed by stirring for 1 hour. Thereafter, water was added to the reaction mixture on an ice bath, and extraction was performed with hexane:ethyl acetate=2:1. The resulting organic phase was washed with an aqueous saturated sodium chloride solution and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→8:2) to obtain the title compound (1.75 g) having the following physical property values.

후처리

  1. extractionextraction
  2. washThe resulting organic phase was washed with an aqueous saturated sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationfollowed by concentration under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→8:2)

출처 및 근거

ORD 기록
ord-4bb030380e974bc88169e9b0d50458a6
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09353113B2

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