Sodium Iodide → HCID 86704358, compound

HRID 1525752Notes

Reaction equation

HRID 1525752 reaction equation
Cl[CH2:2][C:3]#[C:4][CH2:5][OH:6].[C:7]([O:16][CH3:17])(=[O:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[CH:14].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>[Cu]I.CN(C=O)C>[OH:6][CH2:5][C:4]#[C:3][CH2:2][C:14]#[C:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]([O:16][CH3:17])=[O:15]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2027752-Butyn-1-ol, 4-chloro-HCID 5540837-Octynoic acid methyl ester

Product 1

HCID 86704358HCID 86704358, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
30 °C

Procedure

23.00 g (0.22 mol) of 4-chloro-2-butyn-1-ol (I), 33.93 g (0.22 mol) of methyl 7-octynoate (II), 30.41 g (0.22 mol) of K2CO3, 32.98 g (0.22 mol) of NaI, and 20.95 g (0.11 mol) of CuI were added to 440 ml of DMF, followed by stirring at 30° C. for 48 hours. The reaction mixture was quenched by adding to a saturated aqueous NH4Cl solution (200 ml) (hereinafter, referred to as “sat. NH4Cl aq.”), then the resulting mixture was extracted with ethyl acetate. The extract was washed with water, concentrated, and the concentrate was purified over a silica gel column (hexane/ethyl acetate=8/2 to 4/6 (volume ratio)) to obtain 30.97 g of methyl 12-hydroxydodeca-7,10-diynoate having a GC purity of 93.3% (yield: 59.1% th). The structure thereof was confirmed by NMR.

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding to a saturated aqueous NH4Cl solution (200 ml) (hereinafter,
  3. extractionwas extracted with ethyl acetate
  4. washThe extract was washed with water
  5. concentrationconcentrated
  6. customthe concentrate was purified over a silica gel column (hexane/ethyl acetate=8/2 to 4/6 (volume ratio))

Sources & evidence

ORD record
ord-dbf192bd41434d85a45395fab143e430
Source dataset
uspto-grants-2015_07
Patent number
US09085545B2

Reaction notes

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