Bis(trimethylsilylmethyl) sulfoxide → 5-(4'-Chloro-4-ethylbiphenyl-3-yl)-tetrahydrocyclopenta[c]thiophene-4,6-dione

HRID 40473ノート

反応式

HRID 40473 の反応式
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]2[CH:7]=[CH:8][C:9]([CH2:19][CH3:20])=[C:10]([CH:12]3[C:16](=[O:17])[CH:15]=[CH:14][C:13]3=[O:18])[CH:11]=2)=[CH:4][CH:3]=1.C[Si]([CH2:27][S:28]([CH2:30][Si](C)(C)C)=O)(C)C>CN1CCCN(C)C1=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2[CH:7]=[CH:8][C:9]([CH2:19][CH3:20])=[C:10]([CH:12]3[C:16](=[O:17])[CH:15]4[CH2:27][S:28][CH2:30][CH:14]4[C:13]3=[O:18])[CH:11]=2)=[CH:21][CH:22]=1

参加物

4

反応物 2

HCID 13694173Bis(trimethylsilylmethyl) sulfoxideHCID 497657352-(4'-Chloro-4-ethylbiphenyl-3-yl)cyclopent-4-ene-1,3-dione

生成物 1

HCID 497657365-(4'-Chloro-4-ethylbiphenyl-3-yl)-tetrahydrocyclopenta[c]thiophene-4,6-dione

試薬・触媒・溶媒 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-溶媒

反応条件

温度
100 °C

実験手順

A suspension of 2-(4′-chloro-4-ethylbiphen-3-yl)cyclopent-4-ene-1,3-dione (0.200 g, 0.65 mmol) and crude bis(trimethylsilylmethyl)sulphoxide (0.406 g, 0.97 mmol) in 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (3 ml) is heated at 100° C. for 20 minutes under microwave irradiation. The reaction mixture is then partitioned between diethylether and distilled water, and the organic phase is washed with water (×2) then brine. After drying over magnesium sulfate the crude mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is purified by preparative reverse phase HPLC to afford 5-(4′-chloro-4-ethylbiphenyl-3-yl)-tetrahydrocyclopenta[c]thiophene-4,6-dione.

後処理

  1. customThe reaction mixture is then partitioned between diethylether
  2. distillationdistilled water
  3. washthe organic phase is washed with water (×2)
  4. dry with materialAfter drying over magnesium sulfate the crude mixture
  5. filtrationis filtered
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customThe residue is purified by preparative reverse phase HPLC

出典と根拠

ORDレコード
ord-f1dd7b843eee4992a79052391d8a5eed
出典データセット
uspto-grants-2013_09
特許番号
US08530388B2

反応ノート

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