Ethylene Glycol → Methyl 3-(2-methyl-1,3-dioxolan-2-yl)tricyclo[3.3.1.03,7]nonane-1-carboxylate

HRID 1015507Notes

Reaction equation

HRID 1015507 reaction equation
[C:1]([C:4]12[CH2:11][CH:10]3[CH2:12][C:6]([C:13]([O:15][CH3:16])=[O:14])([CH2:7][CH:8]1[CH2:9]3)[CH2:5]2)(=[O:3])[CH3:2].[CH2:17](O)[CH2:18][OH:19].CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[CH3:2][C:1]1([C:4]23[CH2:11][CH:10]4[CH2:12][C:6]([C:13]([O:15][CH3:16])=[O:14])([CH2:7][CH:8]2[CH2:9]4)[CH2:5]3)[O:19][CH2:18][CH2:17][O:3]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 67017872Methyl 3-acetyltricyclo[3.3.1.03,7]nonane-1-carboxylate

Product 1

HCID 67017820Methyl 3-(2-methyl-1,3-dioxolan-2-yl)tricyclo[3.3.1.03,7]nonane-1-carboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of methyl 3-acetyltricyclo[3.3.1.03,7]nonane-1-carboxylate (2.0 g, 8.9 mmol) obtained in step II, 1,2-ethanediol (8.9 mL), p-TSA (47 mg, 5 mol %) and benzene (36 mL) was refluxed using a Dean-Stark apparatus for 1 h. The reaction mixture was cooled to room temperature, 10% aq. NaHCO3 (36 mL) was added, and the two layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, and the solvent was evaporated under reduced pressure to obtain methyl 3-(2-methyl-1,3-dioxolan-2-yl)tricyclo[3.3.1.03,7]nonane-1-carboxylate (2.2 g) in 93% yield as viscous liquid. m/z (M+1) 267. IR cm−1 2954, 1731, 1698, 1460, 1236, 1046, 752. 1H NMR (CDCl3) 300 MHz δ 4.07-3.94 (m, 4H), 3.66 (s 3-H), 2.44-2.36 (m 2-H), 2.27-2.18 (m, 1H), 2.12-2.02 (m, 1H), 1.94-1.81 (m, 8-H), 1.30 (s, 3H).

Workup

  1. temperaturewas refluxed
  2. customfor 1 h
  3. customthe two layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3b7fb070c42647759cb0a128be0bfcdc
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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