Ethyl Bromide → Diethyl 1-(ethyloxy)-4-hydroxy-2,3-naphthalenedicarboxylate

HRID 222429ノート

反応式

HRID 222429 の反応式
Br[CH2:2][CH3:3].[OH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:2]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH3:3]

参加物

5

反応物 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 431092,3-Diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate

生成物 1

HCID 58012479Diethyl 1-(ethyloxy)-4-hydroxy-2,3-naphthalenedicarboxylate収率 60.5%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Bromoethane (0.359 g, 3.29 mmol) was added to a stirred solution of diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate (1 g, 3.29 mmol) and potassium carbonate (0.454 g, 3.29 mmol) in acetone (25 ml). The reaction mixture was refluxed for 24 hours under an atmosphere of argon. The resulting mixture was evaporated and the residue was partitioned between 2× ethylacetate and water. The combined organics were washed with water and dried over magnesium sulphate. The orange oil was purified by chromatography on silica gel, eluting with ethyl acetate (0-10%) in hexane to give the title compound as a clear oil (0.661 g, 1.99 mmol). LC/MS: Rt=3.63, [MH]− 331.

後処理

  1. temperatureThe reaction mixture was refluxed for 24 hours under an atmosphere of argon
  2. customThe resulting mixture was evaporated
  3. customthe residue was partitioned between 2× ethylacetate and water
  4. washThe combined organics were washed with water
  5. dry with materialdried over magnesium sulphate
  6. customThe orange oil was purified by chromatography on silica gel
  7. washeluting with ethyl acetate (0-10%) in hexane

出典と根拠

ORDレコード
ord-148d4c5c1a5a4172a12879080866651a
出典データセット
uspto-grants-2012_06
特許番号
US08207213B2

反応ノート

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