1-Bromo-3-chloropropane → 6-(3-Chloro-propoxy)-3,4-dihydro-2H-naphthalen-1-one

HRID 2042628

反応式

HRID 2042628 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.Br[CH2:14][CH2:15][CH2:16][Cl:17].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:17][CH2:16][CH2:15][CH2:14][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2

参加物

5

反応物 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

生成物 1

HCID 220232326-(3-Chloro-propoxy)-3,4-dihydro-2H-naphthalen-1-one

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

In a 500 mL round bottom flask, 6-hydroxy-3,4-dihydro-2H-naphthalen-1-one (10 g, 61.0 mmol), 1-bromo-3-chloro-propane (9.6 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, dried over MgSO4. Purification with silica gel chromatography eluting with hexanes/ethyl acetate (3:1) produced 10.6 g (73%). Mp 85-87° C. MS m/z 239 (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 10.6 g (73%)

出典と根拠

ORDレコード
ord-2a3ad35a01c24959933e317300ca6f8b
出典データセット
uspto-grants-2013_11
特許番号
US08586588B2

関連ノート

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