Potassium tert-butoxide → HCID 66619363, compound

HRID 417098Notes

Reaction equation

HRID 417098 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH:4]([O:8][C:9]1[CH:10]=[N:11][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:14]=1)[CH2:5][CH2:6]Br.CC(C)([O-])C.[K+]>O1CCCC1>[CH3:1][O:2][C:3]([C:4]1([O:8][C:9]2[CH:10]=[N:11][C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][CH:14]=2)[CH2:6][CH2:5]1)=[O:23]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 66619387HCID 66619387, compound

Product 1

HCID 66619363HCID 66619363, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of 0.55 g (1.45 mmol) 2-(6-benzyloxy-pyridin-3-yloxy)-4-bromo-butyric acid methyl ester in 8 mL tetrahydrofuran was cooled to 0° C. and 0.17 g (1.5 mmol) potassium tert-butoxide were added. The resulting pale yellow solution was stirred for 3 h at room temperature and then poured onto water. The aqueous phase was extracted three times with ethyl acetate and the organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated to give the product as a colorless oil (92%) which was pure enough for the next step. MS (Turbo Spray): m/z=210.1 [M+H].

Workup

  1. additionpoured onto water
  2. extractionThe aqueous phase was extracted three times with ethyl acetate
  3. washthe organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6698fb6709e44261a4cf0b7f1db4e102
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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