Methanol → HCID 86706179, compound

HRID 2176330Notes

Reaction equation

HRID 2176330 reaction equation
C([O:3][C:4]([C:6]1([CH:14]=[CH2:15])[CH2:11][O:10][C:9]([CH3:13])([CH3:12])[O:8][CH2:7]1)=[O:5])C.O.[OH-].[Li+].CO>O1CCCC1.O>[CH3:12][C:9]1([CH3:13])[O:10][CH2:11][C:6]([CH:14]=[CH2:15])([C:4]([OH:5])=[O:3])[CH2:7][O:8]1

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 86706155HCID 86706155, compound

Product 1

HCID 86706179HCID 86706179, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 2,2-dimethyl-5-vinyl-[1,3]dioxane-5-carboxylic acid ethyl ester (150 mg, 0.7 mmol) in tetrahydrofuran (3 mL) was stirred at 5° C. under nitrogen. A solution of lithium hydroxide monohydrate (59 mg, 1.4 mmol) in water (1 mL) was added and the reaction mixture was stirred at 5° C. for 30 minutes and then at room temperature for 5 hours. Methanol (0.5 mL) was added to give a clear solution and the reaction mixture was stirred at room temperature for 22 hours. The solvent was evaporated. Water (2 mL) was added to the residue and the solution was acidified to pH 2 with 2 M hydrochloric acid. Brine was added and the mixture was extracted with ethyl acetate. The organic extracts were combined, washed with brine. The organic extract was separated, washed with water (×5), and brine. The organic solution was filtered through a hydrophobic frit and the filtrate was evaporated to afford the title compound (117 mg, 90%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 1.44 (s, 3H), 1.49 (s, 3H), 3.91 (d, J=12.0 Hz, 2H), 4.32 (d, J=12.0 Hz, 2H), 5.30 (d, J=17.8 Hz, 1H), 5.35 (d, J=10.7 Hz, 1H), 5.76 (dd, J=17.8, 10.7 Hz, 1H). LCMS (m/z) 185.1 [M−H], Tr=1.26 min.

Workup

  1. waitat room temperature for 5 hours
  2. customto give a clear solution
  3. stirringthe reaction mixture was stirred at room temperature for 22 hours
  4. customThe solvent was evaporated
  5. additionWater (2 mL) was added to the residue
  6. additionBrine was added
  7. extractionthe mixture was extracted with ethyl acetate
  8. washwashed with brine
  9. extractionThe organic extract
  10. customwas separated
  11. washwashed with water (×5), and brine
  12. filtrationThe organic solution was filtered through a hydrophobic frit
  13. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-b398da1fdeaf4b629b3053ac1d485bd1
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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