Hydrochloric Acid → HCID 86706144, compound

HRID 2176296Notes

Reaction equation

HRID 2176296 reaction equation
C([O:3][C:4]([CH:6]([O:11][C:12](=[O:18])[C:13]([CH3:17])([CH3:16])[CH:14]=[CH2:15])[CH:7]1[CH2:10][O:9][CH2:8]1)=[O:5])C.C(=O)([O-])[O-].[K+].[K+].CO.Cl>O1CCCC1.O>[C:4]([CH:6]([O:11][C:12](=[O:18])[C:13]([CH3:17])([CH3:16])[CH:14]=[CH2:15])[CH:7]1[CH2:10][O:9][CH2:8]1)([OH:5])=[O:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 86706143HCID 86706143, compound

Product 1

HCID 86706144HCID 86706144, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2,2-dimethyl-but-3-enoic acid ethoxycarbonyl-oxetan-3-yl-methyl ester (207 mg, 0.808 mmol) in tetrahydrofuran (81 mL) was added a solution of potassium carbonate (123 mg, 0.888 mmol) in water (20.25 mL) followed by methanol (4.05 mL). The reaction mixture was heated to reflux for 7 h and then allowed to cool. Hydrochloric acid (2 M, 400 μL) was added (pH 7) and the solvents were evaporated. The residue was extracted with dichloromethane (2×) and the washes discarded. The aqueous was acidified with hydrochloric acid (2 M) to pH 5, extracted with dichloromethane (2×) and the combined organic extracts passed through a hydrophobic frit and evaporated. To the aqueous layer was added hydrochloric acid (about 5 drops) and the mixture was extracted with dichloromethane (2×) and the combined organic extracts passed through a hydrophobic frit, evaporated and combined with previous material to give the title compound (123 mg, 67%) as a yellow/green oil. 1H NMR (300 MHz, CDCl3) δ 1.39 (s, 3H), 1.40 (s, 3H), 3.54-3.67 (m, 1H), 4.67-4.75 (m, 2H), 4.81-4.92 (m, 2H), 5.14 (d, J=10.9 Hz, 1H), 5.15-5.32 (m, 2H), 6.08 (dd, J=17.5, 10.5 Hz, 1H), 9.30 (br s, 1H). LCMS (m/z) 229.1 [M+H] Tr=1.67 min.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 7 h
  3. temperatureto cool
  4. customthe solvents were evaporated
  5. extractionThe residue was extracted with dichloromethane (2×)
  6. extractionextracted with dichloromethane (2×)
  7. customevaporated
  8. additionTo the aqueous layer was added hydrochloric acid (about 5 drops)
  9. extractionthe mixture was extracted with dichloromethane (2×)
  10. customevaporated

Sources & evidence

ORD record
ord-f630c8670ddf4e02a496950e6bdb0b20
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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