Benzyl Bromide → Diethyl 1-(ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylate

HRID 222430ノート

反応式

HRID 222430 の反応式
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([OH:22])=[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:13]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:9]([O:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([O:22][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:13]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH3:10]

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 58012479Diethyl 1-(ethyloxy)-4-hydroxy-2,3-naphthalenedicarboxylate

生成物 1

HCID 58012512Diethyl 1-(ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylate収率 98%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Benzyl bromide (1.32 ml, 11.1 mmol) was added to a stirred solution of diethyl 1-(ethyloxy)-4-hydroxy-2,3-naphthalenedicarboxylate (2.45 g, 7.38 mmol) and potassium carbonate (1.53 g, 11.1 mmol) in acetone (50 ml). The reaction mixture was refluxed for 1 hour under an atmosphere of argon. The resulting mixture was evaporated and the residue was partitioned between 2× ethylacetate and brine. The combined organics were washed with water and dried over magnesium sulphate. The clear oil was purified by chromatography on silica gel, eluting with ethyl acetate (0-40%) in hexane to give the title compound as clear oil (3.05 g, 7.23 mmol). LC/MS: Rt=3.77, [MH]+ 423.

後処理

  1. temperatureThe reaction mixture was refluxed for 1 hour under an atmosphere of argon
  2. customThe resulting mixture was evaporated
  3. customthe residue was partitioned between 2× ethylacetate and brine
  4. washThe combined organics were washed with water
  5. dry with materialdried over magnesium sulphate
  6. customThe clear oil was purified by chromatography on silica gel
  7. washeluting with ethyl acetate (0-40%) in hexane

出典と根拠

ORDレコード
ord-24779be5cc5e471c8a61f4caef005068
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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