6-Methoxy-1-benzothiophene → Benzo(b)thiophene-6-ol

HRID 748949

反応式

HRID 748949 の反応式
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[CH:9][S:8][C:7]=2[CH:11]=1.[Na].C(S)C>CN(C=O)C>[S:8]1[CH:9]=[CH:10][C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:11][C:7]1=2

参加物

4

反応物 2

HCID 136342376-Methoxy-1-benzothiopheneHCID 45051917HCID 45051917、化合物2 回

生成物 1

HCID 88004Benzo(b)thiophene-6-ol収率 36.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

Dissolve 6-methoxy-benzo[b]thiophene (J. Med. Chem. 32:2548, 1989; 26.1 g, 146 mmol) in DMF (500 mL). Add ethanethiol sodium salt (37 g, 440 mmol) and heats to 150° C. with stirring overnight. Add additional ethanethiol sodium salt (112.8 g, 152 mmol) and continue to heat at 150° C. overnight. Concentrate in vacuo to ¼ volume. Partition reaction mixture between ethyl acetate (500 mL) and water (500 mf), separate layers, wash organic layer with water (2×500 mL), brine (500 mL), and dry with magnesium sulfate. Filter and concentrate in vacuo to give 8 g of benzo[b]thiophen-6-ol. Back extract aqueous layers with ethyl acetate (3×1000 mL) wash organics with brine, and dry with magnesium sulfate. Concentrate in vacuo to obtain an additional 15 grams of benzo[b]thiophen-6-ol. Distill off remaining DMF to yield 22.7 g (100%) of benzo[b]thiophen-6-ol.

後処理

  1. customheats to 150° C.
  2. concentrationConcentrate in vacuo
  3. customPartition
  4. customreaction mixture between ethyl acetate (500 mL) and water (500 mf)
  5. customseparate layers
  6. washwash organic layer with water (2×500 mL), brine (500 mL)
  7. dry with materialdry with magnesium sulfate
  8. filtrationFilter
  9. concentrationconcentrate in vacuo

出典と根拠

ORDレコード
ord-1a9dd29be33747dfb270fc730af6dd47
出典データセット
uspto-grants-2008_07
特許番号
US07399867B2

関連ノート

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