Methanol → Tert-butyl 3-(3-ethynylphenethoxy)propanoate

HRID 909890Notes

Reaction equation

HRID 909890 reaction equation
C(=O)([O-])[O-].[K+].[K+].C[Si]([C:11]#[C:12][C:13]1[CH:14]=[C:15]([CH:28]=[CH:29][CH:30]=1)[CH2:16][CH2:17][O:18][CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])(C)C.CO>C(Cl)Cl.O>[C:12]([C:13]1[CH:14]=[C:15]([CH:28]=[CH:29][CH:30]=1)[CH2:16][CH2:17][O:18][CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:22])#[CH:11]

Participants

6

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 67076241Tert-butyl 3-(3-((trimethylsilyl)ethynyl)phenethoxy)propanoate

Product 1

HCID 86641259Tert-butyl 3-(3-ethynylphenethoxy)propanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Potassium carbonate (1.20 g) was added in one portion to tert-butyl 3-(3-((trimethylsilyl)ethynyl)phenethoxy)propanoate [Example 4, Step i)] (2.09 g) in DCM (20 mL) and methanol (20 mL) at 25° C. under nitrogen. The resulting mixture was stirred at 25° C. for 1 h. The reaction mixture was diluted with water and extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered and evaporated to afford tert-butyl 3-(3-ethynylphenethoxy)propanoate (1.65 g). 1H NMR (300 MHz, CDCl3) δ 7.38-7.30 (m, 2H), 7.25-7.18 (m, 2H), 3.68 (t, J=6.5 Hz, 2H), 3.64 (t, J=7.0 Hz, 2H), 3.05 (s, 1H), 2.85 (t, J=7.2 Hz, 2H), 2.48 (t, J=6.4 Hz, 2H), 1.44 (s, 9H).

Workup

  1. customat 25° C.
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-26299ffa72a44f9b89010eac2fdcb4fd
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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