Iodine → HCID 178471365, compound

HRID 1055182

Reaction equation

HRID 1055182 reaction equation
[Zn:1].II.[Br:4]CCCCCCCCC(OCC)=O.[C:18]([O:28][CH2:29][CH3:30])(=[O:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>CC(N(C)C)=O>[Br:4][Zn:1][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:18]([O:28][CH2:29][CH3:30])=[O:27]

Participants

6

Reactant 4

HCID 807Iodine2×HCID 23994Zinc2×HCID 31251Ethyl NonanoateHCID 560317Disodium acetylide

Product 1

HCID 178471365HCID 178471365, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

In a dry reaction tube under nitrogen were charged zinc dust (3.70 g, 56.6 mmol), iodine (479 mg, 1.89 mmol) and dry DMA (20 mL). The mixture was stirred at room temperature until the color of iodine disappeared. Ethyl 9-bromononanoate was added, and the mixture was stirred at 80° C. for 4 hours and then at room temperature overnight. (Completion of the zinc insertion reaction was checked by GCMS analysis of the hydrolyzed reaction mixture.) The reaction mixture was used without further treatment in the subsequent step. GCMS m/z 186 [M]+ (ethyl nonanoate).

Workup

  1. customIn a dry reaction tube under nitrogen
  2. customat room temperature
  3. customovernight

Sources & evidence

ORD record
ord-0ef785149a124889a3ddb5d4f53c3659
Source dataset
uspto-grants-2016_07
Patent number
US09393315B2

Linked notes

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