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

HRID 2193812Notes

Reaction equation

HRID 2193812 reaction equation
OS(O)(=O)=O.[S:6]1[CH:10]=[CH:9][C:8]([C:11](O)([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:12][CH:13]([CH3:15])[CH3:14])=[C:7]1[C:21]1[S:22][CH:23]=[CH:24][CH:25]=1.C(Cl)Cl>O>[CH2:12]([C:11]1([CH2:16][CH:17]([CH3:19])[CH3:18])[C:25]2[CH:24]=[CH:23][S:22][C:21]=2[C:7]2[S:6][CH:10]=[CH:9][C:8]1=2)[CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 585680054-(2,2'-Bithiophene-3-yl)-2,6-dimethylheptan-4-ol

Product 1

HCID 498401464,4-Diisobutyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

H2SO4 (1.45 mL) was added dropwise to 4-(2,2′-bithiophene-3-yl)-2,6-dimethylheptan-4-ol (IIb) (0.688 g, 2.23 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 (Ib) (0.240 g, 35.0%). 1H-NMR (CDCl3): δ=7.12 (d, J=4.8 Hz, 2H), 6.92 (d, J=4.8 Hz, 2H), 1.85 (d, J=5.8 Hz, 4H), 1.08-0.78 (m, 2H), 0.50 (d, J=7.1 Hz, 12H). 13C-NMR (CDCl3): δ=158.45, 137.29, 124.99, 122.66, 53.69, 49.30, 25.46, 25.14.

Workup

  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 (Ib) (0.240 g, 35.0%)

Sources & evidence

ORD record
ord-65912824d54747a193122a4ba05f0c4d
Source dataset
uspto-grants-2012_12
Patent number
US08329923B2

Reaction notes

Loading…