Ethylene Oxide → 2-(2-Triisopropylsilanyloxy-naphthalen-1-yl)-ethanol

HRID 1814336Notes

Reaction equation

HRID 1814336 reaction equation
C([Li])CCC.Br[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[O:17][Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20].[CH2:28]1[O:30][CH2:29]1.B(F)(F)F.CCOCC>CCOCC>[CH:19]([Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[O:17][C:8]1[CH:9]=[CH:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]=1[CH2:28][CH2:29][OH:30])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 6354Ethylene OxideHCID 8000Boron trifluoride etherateHCID 22504240(1-Bromo-naphthalen-2-yloxy)-triisopropyl-silaneHCID 178418339Butyllithium2×

Product 1

HCID 225040152-(2-Triisopropylsilanyloxy-naphthalen-1-yl)-ethanolYield 53%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (16.4 mL of 1.6 M soln in hexanes, 26.3 mmol) was stirred with Et2O (60 mL) at −78° C. in an argon-purged, round-bottom flask. A solution of (1-bromo-naphthalen-2-yloxy)-triisopropyl-silane (7.10 g, 18.8 mmol) in Et2O (˜5 ml) was added dropwise to the stirring n-BuLi solution. The reaction was stirred at −78° C. for ten minutes and then a solution of ethylene oxide (1.41 mL, 28.2 mmol) and BF3-Et2O (3.81 mL, 31.0 mmol) in Et2O (˜5 ml) was added via syringe. The reaction was stirred at −78° C. for one hour and then at room temperature for two hours. The reaction was carefully quenched with H2O and was extracted three times with EtOAc. The organic extracts were combined, washed with brine solution, dried over Na2SO4, filtered through celite, and concentrated. The crude product was purified by gradient elution flash chromatography (SiO2, 100% hexanes to 10% EtOAc-hexanes) to give 2-(2-triisopropylsilanyloxy-naphthalen-1-yl)-ethanol (3.41 g, 9.91 mmol) as a colorless oil in 53% yield. MS (APCI) m/z 343.2 (M−1).

Workup

  1. custompurged
  2. stirringThe reaction was stirred at −78° C. for one hour
  3. customThe reaction was carefully quenched with H2O
  4. extractionwas extracted three times with EtOAc
  5. washwashed with brine solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered through celite
  8. concentrationconcentrated
  9. customThe crude product was purified by gradient elution flash chromatography (SiO2, 100% hexanes to 10% EtOAc-hexanes)

Sources & evidence

ORD record
ord-8eb0ad6b3ca048bf9b5a1318cc9004c8
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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