Diethyl Ether → HCID 67296674, compound

HRID 1969380Notes

Reaction equation

HRID 1969380 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C@H:9]1[O:13][C:12](=[O:14])[CH2:11][CH2:10]1.[CH3:15][CH2:16][Mg+].[Br-].CCOCC>C1COCC1.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[OH:13][C@H:9]([CH2:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH2:10][CH2:11][C:12]1([OH:14])[CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 15482800HCID 15482800, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 67296674HCID 67296674, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 178460666HCID 178460666, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
15 °C

Procedure

To a mixture of Ti(OiPr)4 (0.33 mL, 0.001 mol, Ardrich) and (5S)-5-((tetrahydro-2H-pyran-2-yloxy)methyl)-dihydrofuran-2(3H)-one (1.0 g, 0.005 mol) in 18.7 mL of THF was added a solution of 3M EtMgBr in Et2O (4.3 mL, 0.0125 mol, Aldrich) via a syringe over 3 hrs at 15° C. After stirring for additional one hour at 15° C., the reaction was quenched with 20 mL of saturated NH4Cl solution, filtered and extracted with EtOAc (50 mL×2). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography to afford 1-((S)-3-hydroxy-4-(tetrahydro-2H-pyran-2-yloxy)butyl)cyclopropanol as colorless oil (0.853 g, 74%)2.

Workup

  1. customthe reaction was quenched with 20 mL of saturated NH4Cl solution
  2. filtrationfiltered
  3. extractionextracted with EtOAc (50 mL×2)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-f0ba89ca56514c8e9f6e3b2c079c43f8
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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