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Potassium Carbonate → 6-(3-Thienylmethoxy)-1,3-benzoxathiol-2-one

HRID 322947
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HRID 322947 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[S:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][C:20]1[CH:24]=[CH:23][S:22][CH:21]=1>CN(C)C=O>[S:22]1[CH:23]=[CH:24][C:20]([CH2:19][O:1][C:2]2[CH:11]=[CH:10][C:5]3[S:6][C:7](=[O:9])[O:8][C:4]=3[CH:3]=2)=[CH:21]1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 721396-Hydroxy-1,3-benzoxathiol-2-oneHCID 124874623-(Chloromethyl)thiophene

생성물 1

HCID 220104656-(3-Thienylmethoxy)-1,3-benzoxathiol-2-one수율 37.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 6-hydroxy-1,3-benzoxathiol-2-one (15 g) and potassium carbonate (13.8 g) in dimethylformamide (200 mL) is stirred for 20 minutes, and is then treated, dropwise, with 3-chloromethylthiophene (11.8 g). The mixture is stirred at 60° C. for 16 hours. The reaction mixture is then concentrated in vacuo, and partitioned between water (200 mL) and ethyl acetate (200 mL). The aqueous layer is extracted with ethyl acetate (100 mL) and with diethyl ether (100 mL), and the combined aqueous layers are washed with brine, dried over magnesium sulphate, and evaporated to give a yellow solid, which is recrystallised from ethanol (200 mL) to give 6-(3-thienylmethoxy)-1,3-benzoxathiol-2-one (8.9 g), in the form of pale yellow crystals.

후처리

  1. additionis then treated
  2. stirringThe mixture is stirred at 60° C. for 16 hours
  3. concentrationThe reaction mixture is then concentrated in vacuo
  4. custompartitioned between water (200 mL) and ethyl acetate (200 mL)
  5. extractionThe aqueous layer is extracted with ethyl acetate (100 mL) and with diethyl ether (100 mL)
  6. washthe combined aqueous layers are washed with brine
  7. dry with materialdried over magnesium sulphate
  8. customevaporated
  9. customto give a yellow solid, which
  10. customis recrystallised from ethanol (200 mL)

출처 및 근거

ORD 기록
ord-d339c431f09948629813eca16e91aff5
출처 데이터셋
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06211234B1

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