Triethylamine → HCID 11208638, compound

HRID 2227887Notes

Reaction equation

HRID 2227887 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.Cl[Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Si:15]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 28928tert-Butyldimethylsilyl chloride2×HCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 516892Sodium Bicarbonate

Product 1

HCID 11208638HCID 11208638, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 3-(4-hydroxyphenyl)propionate (5 g, 27.7 mmol) and chlorotert-butyldimethylsilane (5 g, 33.3 mmol) in DMF was treated with triethylamine (4.6 ml). The mixture was stirred at room temperature for 20 hours. More chlorotert-butyldimethylsilane (0.8 g) and triethylamine (0.8 ml) were added, the resulting mixture was stirred at room temperature for another 2 hours, poured into saturated aqueous sodium bicarbonate (500 ml). The mixture was stirred at room temperature for 5 minutes and extracted with ether. The organic phase was washed with brine, dried over sodiun sulfate and concentrated in vacuo. Bulb-to-bulb distillation gave the title material (7.39 g, 91%) as a colorless oil (b.p. 104-105° C./0.025 mm Hg).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for another 2 hours
  2. stirringThe mixture was stirred at room temperature for 5 minutes
  3. extractionextracted with ether
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodiun sulfate
  6. concentrationconcentrated in vacuo
  7. distillationdistillation

Sources & evidence

ORD record
ord-d31bbb69975b4326869473c40ca4e480
Source dataset
uspto-grants-2002_07
Patent number
US06414179B1

Reaction notes

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