1-Bromo-3-chloropropane → 4-[4-(3-Chloro-propoxy)-phenyl]-4-oxo-butyric acid ethyl ester

HRID 2042625노트

반응식

HRID 2042625 반응식
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)=[O:8])[CH3:2].Br[CH2:18][CH2:19][CH2:20][Cl:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:18][CH2:19][CH2:20][Cl:21])=[CH:13][CH:14]=1)=[O:8])[CH3:2]

참가 물질

5

반응물 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 114359904-(4-Hydroxyphenyl)-4-oxo-butyric acid ethyl ester

생성물 1

HCID 596520284-[4-(3-Chloro-propoxy)-phenyl]-4-oxo-butyric acid ethyl ester

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

In a 1 L round bottom flask, 4-(4-hydroxyphenyl)-4-oxo-butyric acid ethyl ester (8.65 g, 39.0 mmol), 1-bromo-3-chloro-propane (6.1 g, 61.0 mmol), and potassium carbonate (9.3 g, 67.1 mmol) in acetonitrile (300 mL) was heated to reflux 14 h. The reaction was cooled and the solvent concentrated under vacuum. The slurry was partitioned between methylene chloride and water, separated and dried over MgSO4. Purification with silica gel chromatography eluting with hexanes/ethyl acetate (3:1) produced 7.9 g (68%). MS m/z 299 (M+H).

후처리

  1. temperatureto reflux 14 h
  2. temperatureThe reaction was cooled
  3. concentrationthe solvent concentrated under vacuum
  4. customThe slurry was partitioned between methylene chloride and water
  5. customseparated
  6. dry with materialdried over MgSO4
  7. customPurification with silica gel chromatography
  8. washeluting with hexanes/ethyl acetate (3:1)
  9. customproduced 7.9 g (68%)

출처 및 근거

ORD 기록
ord-a39f329cf64342c7b998e957275e03bc
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586588B2

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