Tetrahydrofuran → Methyl 2-allyloctanoate

HRID 1180696Notes

Reaction equation

HRID 1180696 reaction equation
COC(N([C@@H](C1C=CC=CC=1)C)C(=O)[CH:7]([CH2:14][CH:15]=[CH2:16])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=O.[CH3:26][O-:27].[Na+].C1C[O:32][CH2:31]C1>>[CH2:11]([CH:10]([CH2:9][CH2:8][CH2:7][CH2:14][CH2:15][CH3:16])[C:26]([O:32][CH3:31])=[O:27])[CH:12]=[CH2:13]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 69502051N-methyloxycarbonyl-N-(2-allyloctanoyl)-1-(R)-phenylethylamine

Product 1

HCID 23117480Methyl 2-allyloctanoateYield 55%

Procedure

A solution of 0.345 g (1.0 mmol) of N-methyloxycarbonyl-N-(2-allyloctanoyl)-1-(R)-phenylethylamine in 5 ml of THF was cooled to 0° C., 0.386 g (2.0 mmol) of NaOMe (28% solution in methanol) was added, and the mixture was stirred for 22 hours. The reaction was terminated by addition of 2 ml of 1 N hydrochloric acid, and the product was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was quantitated by GC. Thus was obtained 0.109 g (55%) of the title compound.

Workup

  1. customThe reaction was terminated by addition of 2 ml of 1 N hydrochloric acid
  2. extractionthe product was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-33279d8c9f2c4023a10c45151be4af4a
Source dataset
uspto-grants-2007_10
Patent number
US07282605B2

Reaction notes

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