Potassium Iodide → Methyl 2-(4-Tert-Butyldimethylsilyloxymethyl-2-Allylphenoxy)-2-Phenylacetate

HRID 1609524

Reaction equation

HRID 1609524 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([CH2:17][CH:18]=[CH2:19])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1OCCOCCOCCOCCOCCOC1.Br[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[CH2:45][C:46]([O:48][CH3:49])=[O:47].[I-].[K+]>CN(C=O)C>[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:45]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:39]=2)[C:46]([O:48][CH3:49])=[O:47])=[C:12]([CH2:17][CH:18]=[CH2:19])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 2855718-Crown-6HCID 8063364Methyl 2-(2-bromophenyl)acetateHCID 199348384-Tert-butyldimethylsilyloxymethyl-2-allylphenol

Product 1

HCID 19934851Methyl 2-(4-Tert-Butyldimethylsilyloxymethyl-2-Allylphenoxy)-2-PhenylacetateYield 65.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of KH (1.3 eq) in DMF (1 mL) was added a solution of the product of Step C (157 mg, 0.566 mmol) in DMF (1 mL), followed by 18-crown-6 (30 mg; 0.2 eq). The reaction mixture was stirred for 5 minutes at room temperature. A solution of methyl 2-bromophenylacetate (168 mg, 0.735 mmol) in DMF (1 mL) was added, followed by a catalytic amount of potassium iodide. The reaction was heated to 80° C. for 0.5 hours then stirred at room temperature for 16 hours. After concentration in vacuo, the residue was partitioned between water and ethyl acetate. The combined organic layers were washed with water, brine, then dried (MgSO4). After filtration and concentration in vacuo, the residue was chromatographed on silica (MPLC, ethyl acetate/hexanes (5/95)) to afford 158 mg (66%) of the title compound (Rf =0.22, 5% ethyl acetate/hexanes).

Workup

  1. temperatureThe reaction was heated to 80° C. for 0.5 hours
  2. stirringthen stirred at room temperature for 16 hours
  3. concentrationAfter concentration in vacuo
  4. customthe residue was partitioned between water and ethyl acetate
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried (MgSO4)
  7. filtrationAfter filtration and concentration in vacuo
  8. customthe residue was chromatographed on silica (MPLC, ethyl acetate/hexanes (5/95))

Sources & evidence

ORD record
ord-5d493879c1da4411bfa82bc2dfa2911a
Source dataset
uspto-grants-1995_03
Patent number
US05401745

Linked notes

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