Oxalyl chloride → 6-Heptenoyl chloride

HRID 1850011Notes

Reaction equation

HRID 1850011 reaction equation
[C:1]([OH:9])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].C(Cl)(=O)C([Cl:13])=O>C(Cl)Cl.CN(C=O)C>[C:1]([Cl:13])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 707056-Heptenoic acid

Product 1

HCID 108556156-Heptenoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-heptenoic acid (251 μL, 1.85 mmol) in CH2Cl2 (5 mL) at rt was added oxalyl chloride (476 μL, 5.55 mmol) and DMF (1 drop). After stirring for 1 hr, the reaction mixture was concentrated under reduced pressure and put under high vacuum for 15 min. The residual yellow oil was dissolved in CH2Cl2 (3 mL) and used as a stock solution (0.62M) for the subsequent acylation reactions.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. waitput under high vacuum for 15 min
  3. dissolutionThe residual yellow oil was dissolved in CH2Cl2 (3 mL)

Sources & evidence

ORD record
ord-fa161849dd47456fb0d63b6bc7021350
Source dataset
uspto-grants-2015_02
Patent number
US08957056B2

Reaction notes

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