Hydrochloric Acid → HCID 18959428, compound

HRID 1464541Notes

Reaction equation

HRID 1464541 reaction equation
BrC1C=C(O[Si:9]([CH2:14][CH3:15])([CH2:12][CH3:13])[CH2:10][CH3:11])C=CC=1.[CH2:16]([Li])[CH2:17][CH2:18][CH3:19].CCO[C:24]([CH3:26])=[O:25].Cl>C(OCC)C.O>[CH2:10]([Si:9]([CH2:14][CH3:15])([CH2:12][CH3:13])[C:17]1[CH:16]=[C:24]([OH:25])[CH:26]=[CH:19][CH:18]=1)[CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 13201437HCID 13201437, compoundHCID 178418339Butyllithium

Product 1

HCID 18959428HCID 18959428, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

A 500 ml flask equipped with a magnetic stirring bar and a pressure equalizing addition funnel, maintained under static argon atmosphere, was charged with silane (J) (45 g, 157 mmol) dissolved in diethyl ether (100 ml). To this vigorously stirred mixture, maintained at -10° C. in an ice-acetone bath, n-butyllithium (2.5M solution in hexane, 75 ml, 188 mmol) was added dropwise over a period of 20 min. Then the mixture was allowed to warm to room temperature. The reaction was complete in 3 h (TLC, ligroin 950:EtOAc=5:1). The mixture was poured into 250 ml of cold water and acidified with hydrochloric acid. The organic layer was separated and the aqueous layer extracted with 3×75 ml portions of ether. The combined extracts were dried over magnesium sulfate, and solvents removed on a rotary evaporator to yield an orange oil, which on purification by flash chromatography (ligroin 950:Et2O=7:1) furnished 3-triethylsilylphenol (K) (23.7 g, 73% yield) as a pale yellow liquid.

Workup

  1. customA 500 ml flask equipped with a magnetic stirring bar
  2. additionaddition funnel
  3. temperaturemaintained under static argon atmosphere
  4. temperatureto warm to room temperature
  5. customThe organic layer was separated
  6. extractionthe aqueous layer extracted with 3×75 ml portions of ether
  7. dry with materialThe combined extracts were dried over magnesium sulfate, and solvents
  8. customremoved on a rotary evaporator
  9. customto yield an orange oil, which
  10. customon purification by flash chromatography (ligroin 950:Et2O=7:1)

Sources & evidence

ORD record
ord-ead71dce0a9e4a7eb47bf6dabed5f1e9
Source dataset
uspto-grants-1994_04
Patent number
US05306604

Reaction notes

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