Methanol → Methyl 3-(1-adamantyl)propanoate

HRID 1925512

Reaction equation

HRID 1925512 reaction equation
[C:1]12([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.S(=O)(=O)(O)O.[CH3:21]O>>[C:1]12([CH2:11][CH2:12][C:13]([O:15][CH3:21])=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 7134943-(1-Adamantyl)propanoic acid

Product 1

HCID 10889502Methyl 3-(1-adamantyl)propanoate

Procedure

To a solution of Intermediate 46 (2.9 g, 13.98 mmol) in methanol (22.6 mL) was added dropwise sulphuric acid (0.4 mL, 6.94 mmol) during 15 minutes at 0° C. The resulting reaction mixture was refluxed for 2 hours. The solvent was removed under reduced pressure and the crude was partitioned between ethyl acetate and water. The organic layer was washed with a solution of sodium hydrogen carbonate (4%), water and brine. The solvent was removed under reduced pressure and the title compound was obtained as a red oil (2.9 g, 95%) and was used in the next step without further purification.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 2 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe crude was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with a solution of sodium hydrogen carbonate (4%), water and brine
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3925c37641764732a7d426a5ac4b4238
Source dataset
uspto-grants-2012_05
Patent number
US08178679B2

Linked notes

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