Dichloromethane → Methyl (S)-3-benzyloxyheptanoate

HRID 2289379Notes

Reaction equation

HRID 2289379 reaction equation
C(Cl)Cl.ClC(Cl)(Cl)C(=N)O[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH:18][C@@H:19]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:20][C:21]([O:23][CH3:24])=[O:22].FC(F)(F)S(O)(=O)=O>C1CCCCC1>[CH2:8]([O:18][C@@H:19]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:20][C:21]([O:23][CH3:24])=[O:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 62406Trifluoromethanesulfonic acidHCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 10419468methyl (S)-3-hydroxyheptanoate2×

Product 1

HCID 54350224Methyl (S)-3-benzyloxyheptanoateYield 84.5%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
22.5 °C

Procedure

In a 2 flask were charged 275 ml of methylene chloride, 550 ml of cyclohexane, 140 g of benzyl trichloroacetoimidate, and 75 g of methyl (S)-3-hydroxyheptanoate (compound (37), R1 =ethyl), and 6 ml of trifluoromethanesulfonic acid was added thereto over 5 minutes while maintaining at 20 to 25° C., followed by allowing the mixture to react at 35 to 40° C. for 5 hours. The by-produced salt was removed by filtration, and the filtrate was washed with a sodium hydrogencarbonate aqueous solution. The solvent was removed by distillation under reduced pressure, and the residue was distilled under reduced pressure to obtain 99.0 g (78.7%) of the titled compound (b.p.: 105-108° C./0.1 mmHg).

Workup

  1. additionwas added
  2. customto react at 35 to 40° C. for 5 hours
  3. customThe by-produced salt was removed by filtration
  4. washthe filtrate was washed with a sodium hydrogencarbonate aqueous solution
  5. customThe solvent was removed by distillation under reduced pressure
  6. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-cee57e8f3499411293a8ad1a3faa20a4
Source dataset
uspto-grants-2000_07
Patent number
US06093345

Reaction notes

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