Methanol → Methyl 2-(4-tert-butyldimethylsilyloxymethylphenoxy)-3-phenylpropanoate

HRID 2399501Notes

Reaction equation

HRID 2399501 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:21]=[CH:20][C:13]([O:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CO>C1(C)C=CC=CC=1>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:14][CH:15]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 7498Benzyl BromideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 19385670Methyl 2-(4-tert-butyldimethylsilyloxymethylphenoxy)acetate

Product 1

HCID 19385610Methyl 2-(4-tert-butyldimethylsilyloxymethylphenoxy)-3-phenylpropanoateYield 42%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1.00 g (3.23 mmol) of the product of Step B dissolved in 4 mL of toluene was stirred under a N2 atmosphere and cooled to 0° C. with an ice-water bath. To this solution was added 9.68 mL (4.85 mmol) of a 0.5M solution of potassium bis(trimethylsilyl)amide in toluene. After a 15 minute interval, 0.46 mL (3.88 mmol) of benzyl bromide was added and the reaction mixture was allowed to warm to room temperature and stirred 1 hour. Several milliliters of methanol were added to consume excess base, and the reaction was partitioned between ethyl acetate and 1N HCl. The organic layer was separated, washed with saturated NaHCO3, brine, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 15% ethyl acetate/hexane to afford 0.540 g (42%) of the title compound.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred 1 hour
  3. customto consume excess base
  4. customthe reaction was partitioned between ethyl acetate and 1N HCl
  5. customThe organic layer was separated
  6. washwashed with saturated NaHCO3, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified on a silica gel flash chromatography column
  11. washeluted with 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-f1677718c45c429ea1f6e4a6700201ff
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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