Sulfuric Acid → 4-Nonyl-4-methyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene

HRID 2193814노트

반응식

HRID 2193814 반응식
OS(O)(=O)=O.[S:6]1[CH:10]=[CH:9][C:8]([C:11](O)([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH3:12])=[C:7]1[C:23]1[S:24][CH:25]=[CH:26][CH:27]=1.C(Cl)Cl>O>[CH2:13]([C:11]1([CH3:12])[C:27]2[CH:26]=[CH:25][S:24][C:23]=2[C:7]2[S:6][CH:10]=[CH:9][C:8]1=2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 585681592-(2,2'-Bithiophene-3-yl)undecan-2-ol

생성물 1

HCID 498402854-Nonyl-4-methyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene

시약·촉매·용매 1

HCID 962Water용매

실험 절차

H2SO4 (1.33 mL) was added dropwise to 2-(2,2′-bithiophene-3-yl)undecan-2-ol (IIc) (0.70 g, 2.08 mmol) under stirring at room temperature. After stirring for 12 h, CH2Cl2 (15 mL) and water (15 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 a pure dark yellow oil (Ic) (0.106 g, 16.0%). 1H-NMR (CDCl3): δ=7.13 (d, J=4.8 Hz, 2H), 6.94 (d, J=4.9 Hz, 2H), 1.82-1.75 (m, 2H), 1.41 (s, 3H), 1.29-1.07 (m, 14H), 0.84 (t, J=6.6 Hz, 3H). 13C-NMR (CDCl3): δ=160.04, 136.50, 125.27, 121.95, 49.53, 39.66, 32.50, 30.63, 30.36, 30.20, 30.07, 29.91, 25.65, 24.36, 23.32, 14.77.

후처리

  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 a pure dark yellow oil (Ic) (0.106 g, 16.0%)

출처 및 근거

ORD 기록
ord-aa430f8afbbc43b5ba64b26c82a86d00
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329923B2

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