Trimethyl orthoformate → HCID 68863774, compound

HRID 1454765Notes

Reaction equation

HRID 1454765 reaction equation
[C:1]([C:4]12[CH2:13][CH:8]([C:9]([CH3:12])=[CH:10][CH2:11]1)C(=O)[CH2:6][CH:5]2[CH3:15])([CH3:3])=[CH2:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:28][O:29][CH:30](OC)[O:31][CH3:32].C([O-])(O)=O.[Na+]>CO>[C:1]([C:4]12[CH2:13][CH:8]([C:30]([O:31][CH3:32])([O:29][CH3:28])[CH2:15][CH:5]1[CH3:6])[C:9]([CH3:12])=[CH:10][CH2:11]2)([CH3:3])=[CH2:2]

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 68526884HCID 68526884, compound

Product 1

HCID 68863774HCID 68863774, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A soln. of 1.5 g of 5-isopropenyl-4,8-dimethylbicyclo[3.3.1]non-7-en-2-one (7.3 mmol), 1.4 g para-toluenesulfonic acid mono hydrate (7.4 mmol 1 eq.), and 0.78 g trimethylorthoformate (7.4 mmol, 1 eq.) in 50 ml methanol was heated at 60° C. for 66 h. The reaction mixture was then cooled and poured into aq. sat. NaHCO3 soln. (20 ml). Extraction with MTBE (2×80 ml) followed by washing of the aq. phases with H2O and aq. sat. NaCl soln., drying of org. phases (MgSO4) led to 1.8 g of crude product. FC (SiO2, Hexane/MTBE 30:1) gave 1.7 g (92%) of compound 5 as colorless liquid. The boiling point of the end product is 130° C. at 0.08 mbar. Rf (hexane/MTBE 8:1) 0.57.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. extractionExtraction with MTBE (2×80 ml)
  3. washby washing of the aq. phases with H2O and aq. sat. NaCl soln
  4. custom, drying of org

Sources & evidence

ORD record
ord-466d74d2fec84ace9f8e4148ce63b342
Source dataset
uspto-grants-2009_01
Patent number
US07482313B2

Reaction notes

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