Triethylamine → Methyl 3-(tert-butyldimethylsilyloxy)-2,2-dimethylpropanoate

HRID 553841Notes

Reaction equation

HRID 553841 reaction equation
[CH3:1][C:2]([CH3:9])([CH2:7][OH:8])[C:3]([O:5][CH3:6])=[O:4].[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].CCN(CC)CC.OS([O-])(=O)=O.[Na+]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:6][O:5][C:3](=[O:4])[C:2]([CH3:9])([CH3:1])[CH2:7][O:8][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 84152Methyl 3-hydroxypivalateHCID 516919Sodium Bisulfate

Product 1

HCID 12044793Methyl 3-(tert-butyldimethylsilyloxy)-2,2-dimethylpropanoateYield 32.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Methyl 2,2-dimethyl-3-hydroxypropionate (1.32 g), tert-butyldimethylsilyl chloride (1.8 g), 4-dimethylaminopyridine (122 mg) and NEt3 (1.67 ml) were dissolved in DCM (100 ml) and stirred for 16 h at RT. A NaHSO4 solution was added, and the org. phase was further washed with water, dried (Na2SO4) and evaporated off. Column chromatography (EA/Hept 1/4) afforded 800 mg of the desired compound.

Workup

  1. washphase was further washed with water
  2. dry with materialdried (Na2SO4)
  3. customevaporated off

Sources & evidence

ORD record
ord-7360ed879fe54fab90efb37696c567f8
Source dataset
uspto-grants-2011_11
Patent number
US08048881B2

Reaction notes

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