Triethylamine → Ethyl 2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]acetate

HRID 270149Notes

Reaction equation

HRID 270149 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH2:2][OH:3].C(N(CC)CC)C.[CH3:15][C:16]([Si:19](Cl)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:18])[CH3:17]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Si:19]([O:3][CH2:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])([C:16]([CH3:18])([CH3:17])[CH3:15])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12184Ethyl GlycolateHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 59464758Ethyl 2-[[(1,1-dimethylethyl)diphenylsilyl]oxy]acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a 500ml round-bottom flask equipped with a magnetic stir-bar, N2inlet was added ethyl glycolate (10g, 96.0mmoles, 1eq) and dry CH2Cl2(200ml, 0.5M). This was followed by the addition of triethylamine (40ml, 0.288moles, 3eq) and DMAP (1.17g, 9.6mmoles, 10mol %) followed by the dropwise addition of TBDPSCl (27.5ml, 0.106moles, 1.1eq) in dry CH2Cl2(20ml). The reaction mixture was allowed to stir at room temperature overnight at which time the reaction mixture was diluted with CH2Cl2and washed with 1N HCl, saturated sodium bicarbonate, H2O and dried over Na2SO4. After filtration the volatiles were removed in vacuo to yield 30g (91%) of titled compound.

Workup

  1. customTo a 500ml round-bottom flask equipped with a magnetic stir-bar
  2. additionwas diluted with CH2Cl2and
  3. washwashed with 1N HCl, saturated sodium bicarbonate, H2O
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration the volatiles
  6. customwere removed in vacuo

Sources & evidence

ORD record
ord-1bffa4df35c44444abb28d4089f95e54
Source dataset
uspto-grants-2008_11
Patent number
US07449468B2

Reaction notes

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