Potassium Carbonate → HCID 18184970, compound

HRID 1358573Notes

Reaction equation

HRID 1358573 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:14])([OH:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.Br[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:20]([O:19][C:17]([CH2:16][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:14])([OH:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 572033HCID 572033, compound

Product 1

HCID 18184970HCID 18184970, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 4-hydroxyphenyllactate (18.5 g), t-butyl bromoacetate (14 ml), anhydrous potassium carbonate (26.0 g) and anhydrous dimethylformamide (300 ml) was stirred at 60° C. for 10 hours and then allowed to stand at room temperature overnight The reaction mixture was partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using hexane:ethyl acetate=2:1-1:1 as the eluant to afford the title compound (17.5 g, Rf=0.62: thin layer chromatography on a silica gel plate using hexane:ethyl acetate=1:1 as the eluant).

Workup

  1. waitto stand at room temperature overnight
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe extract was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-bcdbb0f95d1448ca8d361eebd4d014bf
Source dataset
uspto-grants-2003_07
Patent number
US06596751B2

Reaction notes

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