Acetic Acid → (E)-2-cyano-oct-2-enoic acid methyl ester

HRID 2100550Notes

Reaction equation

HRID 2100550 reaction equation
C(=O)CC[CH2:4][CH2:5][CH3:6].[NH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.Cl[CH2:15]Cl.[C:17]([OH:20])(=[O:19])C>>[CH3:15][O:20][C:17](=[O:19])/[C:12](/[C:13]#[N:8])=[CH:11]/[CH2:10][CH2:9][CH2:6][CH2:5][CH3:4]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6184HexanalHCID 6344DichloromethaneHCID 8082Piperidine

Product 1

HCID 86616607(E)-2-cyano-oct-2-enoic acid methyl ester

Procedure

Hexanal (6.06 ml, 50 mmol) and piperidine (0.16 ml) were added to a solution of mehtylcyano acetate (4.4 ml, 49 mmol) in acetic acid (6.8 ml). The solution was stirred for 14 h at ambient temperature and poured onto ice water/dichloromethane 1/1. The layers were separated and the aqueous layer was extracted two times with dichloromethane. The combined extracts were washed with ice water, dried over sodium sulfate and the solvent was removed under reduced pressure to yield (E)-2-cyano-oct-2-enoic acid methyl ester as yellow oil (9.66 g, 53 mmol; quant.) which was used in the next step without further purification. MS: m/e=199.1 [M+NH4+].

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted two times with dichloromethane
  3. washThe combined extracts were washed with ice water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0a1dd0e9b16e49378036c3ccdbc9fbcc
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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