Methyl 5-(4-hydroxybutyl)thiophene-2-carboxylate → HCID 59268844, compound

HRID 889073Notes

Reaction equation

HRID 889073 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:8][CH:9]=1)=[O:4].CCCCCC.CC[O:23]C(C)=O>CC(C)=O.S(=O)(=O)(O)O.O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][C:13]([OH:23])=[O:14])=[CH:8][CH:9]=1)=[O:4]

Participants

6

Reactant 2

HCID 14796144Methyl 5-(4-hydroxybutyl)thiophene-2-carboxylateHCID 21226206Ethyl acetate hexane

Product 1

HCID 59268844HCID 59268844, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 3 (1.14 g, 5.3 mmol) in acetone (15 mL) was added dropwise to a cold solution (ice bath) of CrO3 (3 g, 30 mmol) in sulfuric acid (23 mL) and water (67 mL). After the addition, the resulting solution was stirred in an ice bath for an additional 2 h and the solution was allowed to warm to room temperature overnight. TLC indicated the disappearance of the starting alcohol and the formation of one major spot at Rf=0.35 (hexane/EtOAc 2:1). The solution was extracted with 5×30 mL of ethyl ether and dried over Na2SO4. After evaporation of the solvent under reduced pressure, the resulting residue was flash chromatographed through silica gel column (3.5×15 cm) using hexane/EtOAc (2:1) as eluent. The desired fraction (TLC) was collected and the solvent was evaporated under reduced pressure to afford 570 mg of 4 as colorless oil. 1H NMR (DMSO-d6): δ 1.79-1.87 (m, 2H), 2.24-2.27 (t, J=7.2 Hz, 2H), 2.82-2.86 (t, J=7.2 Hz, 2H), 3.77 (s, 3H), 6.95-6.96 (d, J=3.6 Hz, 1H), 7.63-7.64 (d, J=3.6 Hz, 1H), 12.17 (br, 1H). HRMS calcd for C10H12O4S (M+), 228.0456; found: 228.0458.

Workup

  1. additionAfter the addition
  2. extractionThe solution was extracted with 5×30 mL of ethyl ether
  3. dry with materialdried over Na2SO4
  4. customAfter evaporation of the solvent under reduced pressure
  5. customchromatographed through silica gel column (3.5×15 cm)
  6. customThe desired fraction (TLC) was collected
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b6818aecfadd4b35b34a80af2bbb0040
Source dataset
uspto-grants-2012_08
Patent number
US08252804B2

Reaction notes

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