Triethylamine → HCID 18179382, compound

HRID 1358909Notes

Reaction equation

HRID 1358909 reaction equation
[CH:1]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[O:9])[CH2:3][C:2]2=[O:10].C(N(CC)CC)C.[CH3:18][S:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[C:24]([CH3:31])[C:23]=1[CH2:32][O:33][CH3:34])(=[O:21])=[O:20]>C(Cl)Cl>[O:9]=[C:4]1[CH:5]2[CH2:8][CH:1]([CH2:7][CH2:6]2)[C:2]([O:10][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][C:22]([S:19]([CH3:18])(=[O:21])=[O:20])=[C:23]([CH2:32][O:33][CH3:34])[C:24]=2[CH3:31])=[CH:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 144686Bicyclo(3.2.1)octane-2,4-dioneHCID 19804754HCID 19804754, compound

Product 1

HCID 18179382HCID 18179382, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

0.8 g (5.8 mmols) of bicyclo[3.2.1]octan-2,4-dione (the preparation thereof is described for example in U.S. Pat. No. 5,608,101 and in the references cited therein) are dissolved in 15 ml of methylene chloride at 20° C. The solution is mixed with 0.97 ml of triethylamine and cooled to a temperature of 0° C. Then, a solution of 1.6 g (5.8 mmols) of 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid chloride in 10 ml of methylene chloride is added dropwise. The reaction mixture is stirred for half an hour at a temperature of 0° C. and is subsequently diluted with methylene chloride. After washing and drying, the organic phase is concentrated by evaporation. 2.23 g of 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid-4-oxo-bicyclo[3.2.1]oct-2-en-2-yl-ester is obtained in amorphous form. This can be used for the next step without purification.

Workup

  1. washAfter washing
  2. customdrying
  3. concentrationthe organic phase is concentrated by evaporation

Sources & evidence

ORD record
ord-4dcc4ea3753e476288ba85ce0f1516ec
Source dataset
uspto-grants-2003_07
Patent number
US06599861B2

Reaction notes

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