Potassium Carbonate → 3-(5-Chloro-thiophen-2-ylmethoxy)-phthalic acid dimethyl ester

HRID 709581ノート

反応式

HRID 709581 の反応式
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].C(=O)([O-])[O-].[K+].[K+].[Cl:22][C:23]1[S:24][C:25]([CH2:28]Cl)=[CH:26][CH:27]=1>CC(C)=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([O:14][CH2:28][C:25]2[S:24][C:23]([Cl:22])=[CH:27][CH:26]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 5830792-Chloro-5-(chloromethyl)thiopheneHCID 12223651Dimethyl 3-hydroxyphthalate

生成物 1

HCID 669061873-(5-Chloro-thiophen-2-ylmethoxy)-phthalic acid dimethyl ester収率 99.3%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a stirred suspension of 3-hydroxyphthalic acid dimethyl ester (1.4 g, 6.8 mmol) in acetone (70 mL) and potassium carbonate (2.8 g, 20 mmol) was added 2-chloro-5-chloromethyl-thiophene (0.83 mL, 7.1 mmol) and refluxed for two hours. The solvent was evaporated and the residue was partitioned between water (100 mL) and ethyl acetate (150 mL) and washed with water (2×100 mL). The combined organic phases was dried, concentrated and purified by flash column chromatography (EtOAc/Hexane) to give 3-(5-chloro-thiophen-2-ylmethoxy)-phthalic acid dimethyl ester (2.3 g, 100% crude yield). The product was used in the next step without further purification.

後処理

  1. temperaturerefluxed for two hours
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between water (100 mL) and ethyl acetate (150 mL)
  4. washwashed with water (2×100 mL)
  5. customThe combined organic phases was dried
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (EtOAc/Hexane)

出典と根拠

ORDレコード
ord-b8f33f80e41f40628c5e01955c30b2f7
出典データセット
uspto-grants-2015_11
特許番号
US09181216B2

反応ノート

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