2-(Benzyloxy) ethanol → HCID 66730516, compound

HRID 1959974Notes

Reaction equation

HRID 1959974 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:12]1[CH:17]2[CH:13]1[CH2:14][O:15][CH2:16]2.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C@@H:17]1[CH2:16][O:15][CH2:14][C@H:13]1[OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 121412-(Benzyloxy) ethanolHCID 675113,6-Dioxabicyclo[3.1.0]hexaneHCID 516892Sodium Bicarbonate

Product 1

HCID 66730516HCID 66730516, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into dichloromethane (5.0 mL), 2-benzyloxyethanol (7.07 g, 46.5 mmol) and 3,4-epoxytetrahydrofuran (1.0 g, 11.6 mmol) were dissolved, to which a boron trifluoride-diethyl ether complex (0.08 g, 0.58 mmol) was added at room temperature, followed by stirring for three hours. To the resulting reaction liquid, a saturated aqueous solution of sodium bicarbonate was added, followed by extraction with dichloromethane. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-0:100, V/V) to give the desired title compound (2.28 g, yield 82%).

Workup

  1. additionwas added at room temperature
  2. customTo the resulting reaction liquid
  3. extractionfollowed by extraction with dichloromethane
  4. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-0:100, V/V)

Sources & evidence

ORD record
ord-0da7f032506448bfa942365c76d0e346
Source dataset
uspto-grants-2013_04
Patent number
US08410273B2

Reaction notes

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