Sodium Iodide → 2-Methyl-2-(2-methyl-4-pent-4-ynyloxy-phenoxy)-propionic acid ethyl ester

HRID 852374Notes

Reaction equation

HRID 852374 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH3:16])([CH3:7])[CH3:6])[CH3:2].Cl[CH2:19][CH2:20][CH2:21][C:22]#[CH:23].[Na+].[I-].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:17])[C:5]([CH3:6])([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:23][CH2:22][CH2:21][C:20]#[CH:19])=[CH:11][C:10]=1[CH3:16])[CH3:7])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonate2×HCID 843081-Pentyne, 5-chloro-2×HCID 16756990Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoate

Product 1

HCID 866025402-Methyl-2-(2-methyl-4-pent-4-ynyloxy-phenoxy)-propionic acid ethyl esterYield 91.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.95 g (4.0 mmol) 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (described in WO 02/092590) and 0.42 ml (4.0 mmol) 5-chloro-pent-1-yne in 20 ml acetonitrile were added 0.60 g (4.0 mmol) NaI and 1.56 g (4.80 mmol) Cs2CO3. The mixture was stirred at 50° C. for 3 days and every day 0.42 ml (4.0 mmol) 5-chloro-pent-1-yne and 1.56 g (4.80 mmol) Cs2CO3 were added (two times). After 2 further days stirring at ambient temperature and filtration, the solvent was evaporated. The residue was redissolved in dichloromethane, dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (SiO2, n-heptane/EtOAc 2.5 to 5%) yielded 1.11 g of the title compound as colorless oil.

Workup

  1. additionwere added (two times)
  2. filtrationfiltration
  3. customthe solvent was evaporated
  4. dissolutionThe residue was redissolved in dichloromethane
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by flash chromatography (SiO2, n-heptane/EtOAc 2.5 to 5%)

Sources & evidence

ORD record
ord-0bb0e44a45084fd9ae49c46859e5535e
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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