Potassium Carbonate → HCID 57890146, compound

HRID 1819927Notes

Reaction equation

HRID 1819927 reaction equation
[CH2:1]([C:3]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH3:19])[CH:13]=1)([C:6]1[S:7][CH:8]=[C:9]([CH3:11])[CH:10]=1)[CH2:4][CH3:5])[CH3:2].Br[CH2:21][C:22]([O:24][CH3:25])=[O:23].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:25][O:24][C:22](=[O:23])[CH2:21][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:3]([CH2:4][CH3:5])([C:6]2[S:7][CH:8]=[C:9]([CH3:11])[CH:10]=2)[CH2:1][CH3:2])=[CH:13][C:14]=1[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 57890056HCID 57890056, compound

Product 1

HCID 57890146HCID 57890146, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-[1-Ethyl-1-(4-methyl-thiophen-2-yl)-propyl]-2-methyl-phenol (10.66 g, 38.9 mmol) is reacted with methyl bromoacetate (4.4 ml, 46.7 mmol) and K2CO3 (10.70 g, 77.81 mmol) in acetone (100 m) at refluxing temperature overnight. The reaction is cooled to RT, filtered and washed with Et2O and concentrated. The crude product is purified by chromatography to give the titled compound (12.15 g, 35.1 mmol, 90%). 1H NMR (CD3Cl3), δ 0.70 (t, J=7.2 Hz, 6H), 2.04-2.12 (m, 4H), 2.21 (s, 3H), 2.26 (s, 3H), 3.81 (s, 3H), 4.63 (s, 2H), 6.57-6.61 (m, 2H), 6.69-6.71 (m, 1H), 7.02-7.06 (m, 2H). LC/MS (m/z): calcd for C20H27O3S (M+H)+:347.5; found: 347.1.

Workup

  1. temperatureat refluxing temperature overnight
  2. filtrationfiltered
  3. washwashed with Et2O
  4. concentrationconcentrated
  5. customThe crude product is purified by chromatography

Sources & evidence

ORD record
ord-94eb947ad1b74c1fb94e996feda8543f
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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