Ethanol → HCID 49840148, compound

HRID 2193825Notes

Reaction equation

HRID 2193825 reaction equation
OS(O)(=O)=O.[S:6]1[CH:10]=[CH:9][C:8]([C:11]2([CH3:17])[O:15][C:14](=[O:16])[CH2:13][CH2:12]2)=[C:7]1[C:18]1[S:19][CH:20]=[CH:21][CH:22]=1.C(Cl)Cl.O.[CH2:27](O)[CH3:28]>>[CH3:17][C:11]1([CH2:12][CH2:13][C:14]([O:15][CH2:27][CH3:28])=[O:16])[C:22]2[CH:21]=[CH:20][S:19][C:18]=2[C:7]2[S:6][CH:10]=[CH:9][C:8]1=2

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 49840280HCID 49840280, compound

Product 1

HCID 49840148HCID 49840148, compound

Procedure

H2SO4 (0.30 mL) was added dropwise to a solution of 5-([2,2′-bithiophen]-3-yl)-5-methyldihydrofuran-2(3H)-one (0.030 g, 0.11 mmol) in ethanol (2 mL) 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 dichloromethane) to afford a pure dark yellow oil (IIv) (0.0106 g, 31.9%). 1H-NMR (CDCl3): δ=7.15 (d, J=4.9 Hz, 2H), 6.93 (d, J=4.7 Hz, 2H), 3.96 (q, J=7.1 Hz, 2H), 2.28-2.21 (m, 2H), 1.80-1.74 (m, 2H), 1.45 (s, 3H), 1.13 (t, J=7.2 Hz, 3H).

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 dichloromethane)
  8. customto afford a pure dark yellow oil (IIv) (0.0106 g, 31.9%)

Sources & evidence

ORD record
ord-200297ab44264c01b94c05719ee1b770
Source dataset
uspto-grants-2012_12
Patent number
US08329923B2

Reaction notes

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