1,2-Cyclohexanedione → Methyl 3-acetyl-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylate

HRID 240872

反応式

HRID 240872 の反応式
[O:1]=[C:2]([CH3:10])[CH2:3][S:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[Na].[C:12]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=O>CO>[C:2]([C:3]1[S:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:12]=12)(=[O:1])[CH3:10]

参加物

5

反応物 3

HCID 130061,2-CyclohexanedioneHCID 3761561MS-1254HCID 5360545Sodium

生成物 1

HCID 71014115Methyl 3-acetyl-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylate収率 27.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
0 °C

実験手順

Add methyl 2-(2-oxopropylthio)acetate (35.4 g, 183.2 mmol) to a freshly prepared solution of solid sodium (8.78 g, 381.5 mmol) in dry MeOH (300 mL) at 0° C., followed by addition of a solution of cyclohexane-1,2-dione (20 g, 152.6 mmol) in MeOH (30 mL). Stir the mixture at 0° C. for 30 min and then at 50-60° C. for additional 1.5 hour. Remove the solvent under vacuum and dilute the residue with water (100 mL). Extract the aqueous mixture with ethyl acetate (100 mL×3). The combined organic layers are washed with brine, dried over anhydrous Na2SO4, and evaporated under vacuum. Purify the residue by a flash column on silica gel eluting with PE:EtOAc (50:1 to 30:1) to afford methyl 3-acetyl-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylate as a white solid (10 g, 27.6%). MS (m/z): 239 (M+1).

後処理

  1. waitat 50-60° C. for additional 1.5 hour
  2. customRemove the solvent under vacuum
  3. additiondilute the residue with water (100 mL)
  4. extractionExtract the aqueous mixture with ethyl acetate (100 mL×3)
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customevaporated under vacuum
  8. customPurify the residue by a flash column on silica gel eluting with PE

出典と根拠

ORDレコード
ord-16ae45163c034151bc435fb173b7e888
出典データセット
uspto-grants-2014_02
特許番号
US08648081B2

関連ノート

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