Sulfuric Acid → 4,4-Diethyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene

HRID 2193810ノート

反応式

HRID 2193810 の反応式
OS(O)(=O)=O.[S:6]1[CH:10]=[CH:9][C:8]([C:11](O)([CH2:14][CH3:15])[CH2:12][CH3:13])=[C:7]1[C:17]1[S:18][CH:19]=[CH:20][CH:21]=1.C(Cl)Cl>O>[CH2:12]([C:11]1([CH2:14][CH3:15])[C:21]2[CH:20]=[CH:19][S:18][C:17]=2[C:7]2[S:6][CH:10]=[CH:9][C:8]1=2)[CH3:13]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 498402833-(2,2'-Bithiophene-3-yl)pentan-3-ol

生成物 1

HCID 498402844,4-Diethyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

H2SO4 (7.0 mL) was added dropwise to 3-(2,2′-bithiophene-3-yl)pentan-3-ol (IIa) (2.67 g, 11 mmol) under stirring at room temperature. After stirring for 12 h, CH2Cl2 (100 mL) and water (100 mL) were added. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were successively washed with saturated NaHCO3 and brine. After drying over MgSO4, the solvent was removed in vacuo. The crude oil was purified with column chromatography (eluent hexane) to afford pure dark yellow oil (Ia) (1.2 g, 47%). 1H-NMR (CDCl3): δ=7.21 (d, J=4.8 Hz, 2H), 7.00 (d, J=4.8 Hz, 2H), 1.98 (q, J=6.8 Hz), 4H), 0.70 (t, J=7.0 Hz, 6H). 13C-NMR (CDCl3): δ=157.89, 137.36, 125.09, 122.16, 54.76, 30.71, 9.74.

後処理

  1. stirringAfter stirring for 12 h
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. washThe combined organic extracts were successively washed with saturated NaHCO3 and brine
  5. dry with materialAfter drying over MgSO4
  6. customthe solvent was removed in vacuo
  7. customThe crude oil was purified with column chromatography (eluent hexane)
  8. customto afford pure dark yellow oil (Ia) (1.2 g, 47%)

出典と根拠

ORDレコード
ord-3a3dcd1179d2423093038e3fad87901f
出典データセット
uspto-grants-2012_12
特許番号
US08329923B2

反応ノート

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