Methanol → Muskone

HRID 1885762Notes

Reaction equation

HRID 1885762 reaction equation
[C:1]1(=[O:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[CH3:17]O>C1(C)C=CC=CC=1>[CH3:17][CH:14]1[CH2:15][C:1](=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 887MethanolHCID 11074987(2E)-cyclopentadec-2-en-1-one

Product 1

HCID 10947Muskone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 10 ml of dried toluene was dissolved 5 mmol of (E)-2-cyclopentadecenone, and the solution was added dropwise to the above solution, followed by allowing the reaction to proceed at -78° C. to -60° C. for 15 hours. Thereafter, the same procedures as in Example 14 were followed to obtain muscone having an optical rotation of +11.8° (at 21° C., c 5.13, MeOH) and an optical purity of 100 %ee in a chemical yield of 90 mol %.

Workup

  1. additionthe solution was added dropwise to the above solution
  2. customthe reaction

Sources & evidence

ORD record
ord-bbce394e53b0487aae9650b8b977e6ad
Source dataset
uspto-grants-1992_09
Patent number
US05146003

Reaction notes

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