Water → 2-(Oxan-4-yloxy)ethan-1-ol

HRID 2359358Notes

Reaction equation

HRID 2359358 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.O>O1CCCC1>[O:8]1[CH2:9][CH2:10][CH:5]([O:4][CH2:3][CH2:2][OH:1])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 65367Trimethylsilyl triflateHCID 534405191,4,8-Trioxaspiro[4.5]decane

Product 1

HCID 597122412-(Oxan-4-yloxy)ethan-1-olYield 88.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-50 °C

Procedure

1,4,8-Trioxaspiro[4.5]decane (0.43 g, 3.0 mmol) produced in Reference Example 13 (13a) was dissolved in tetrahydrofuran (1.0 mL), and the resulting mixture was cooled to −50° C. Subsequently, a 1.0M solution of borane-tetrahydrofuran complex in tetrahydrofuran (3.6 mL) and trimethylsilyl trifluoromethanesulfonate (33 mg, 0.15 mmol) were added. The resulting mixture was warmed to room temperature, followed by stirring for 18 hours. A small amount of water was added, and then the resulting mixture was purified by basic silica gel column chromatography (hexane:ethyl acetate, 100:0-0:100, V/V) to give the desired title compound (0.39 g, yield 88%).

Workup

  1. temperatureThe resulting mixture was warmed to room temperature
  2. customthe resulting mixture was purified by basic silica gel column chromatography (hexane:ethyl acetate, 100:0-0:100, V/V)

Sources & evidence

ORD record
ord-3223f053d1434c94be049684f29539ab
Source dataset
uspto-grants-2014_04
Patent number
US08685981B2

Reaction notes

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