Methanol → (2-Methyl-4-prop-2-ynylsulfanyl-phenoxy)-acetic acid tert-butyl ester

HRID 852364Notes

Reaction equation

HRID 852364 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16](=O)[CH3:17])=[CH:11][C:10]=1[CH3:19])([CH3:4])([CH3:3])[CH3:2].[CH2:21](Br)C#C.CO.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][CH2:16][C:17]#[CH:21])=[CH:11][C:10]=1[CH3:19])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 11572955(4-Acetylsulfanyl-2-methyl-phenoxy)-acetic acid tert-butyl ester

Product 1

HCID 86602538(2-Methyl-4-prop-2-ynylsulfanyl-phenoxy)-acetic acid tert-butyl esterYield 100.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3.50 g (11.81 mmol) of (4-acetylsulfanyl-2-methyl-phenoxy)-acetic acid tert-butyl ester (example 4A]) and 1.97 ml (17.71 mmol) of propargyl bromide were dissolved in 60 ml of acetonitrile and 3 ml of MeOH and treated with 6.62 g (14.17 mmol) Cs2CO3. After vigorous stirring for 3 h at ambient temperature and filtration, the solvent was evaporated and the residue redissolved in EtOAc. The organic phase was washed with aqueous 1N NaOH (two times) and aqueous 10% NaCl. After extraction of the water phases with EtOAc (two times), the organic phase was dried (Na2SO4) and evaporated to give 3.48 g of the title compound as a yellow oil.

Workup

  1. filtrationfiltration
  2. customthe solvent was evaporated
  3. dissolutionthe residue redissolved in EtOAc
  4. washThe organic phase was washed with aqueous 1N NaOH (two times) and aqueous 10% NaCl
  5. extractionAfter extraction of the water phases with EtOAc (two times)
  6. dry with materialthe organic phase was dried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-d336d8c71c454199a1c8c0296cd90b78
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

Loading…