Oxalyl chloride → 6-Heptenoyl chloride

HRID 76910

Reaction equation

HRID 76910 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-f83d34427ecc4f969b904b95bb6636c5
Source dataset
uspto-grants-2014_09
Patent number
US08835693B2

Linked notes

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