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

HRID 2042625ノート

反応式

HRID 2042625 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-a39f329cf64342c7b998e957275e03bc
出典データセット
uspto-grants-2013_11
特許番号
US08586588B2

反応ノート

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