Sodium hydride → HCID 67296922, compound

HRID 1969396Notes

Reaction equation

HRID 1969396 reaction equation
CS(O[CH2:6][CH:7]([O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1)[CH2:8][C:9]1([OH:12])[CH2:11][CH2:10]1)(=O)=O.[H-].[Na+]>C1COCC1>[O:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH:14]1[O:13][CH:7]1[CH2:8][C:9]2([CH2:11][CH2:10]2)[O:12][CH2:6]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86640793HCID 86640793, compound

Product 1

HCID 67296922HCID 67296922, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(1-hydroxycyclopropyl)-2-(tetrahydro-2H-pyran-2-yloxy)propyl methanesulfonate (1.3 g, 4.63 mmol) and NaH (0.15 g, 6 mmol, Aldrich) in 20 mL of THF was stirred at rt for 4 hrs. The reaction mixture was quenched with 5 mL of methanol. The mixture was diluted with 10 mL of water and extracted with ethyl acetate (30 mL×3). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (1:10 (v/v) EtOAc/petroleum ether) to give the title compound as colorless oil (380 mg, 42%).

Workup

  1. customThe reaction mixture was quenched with 5 mL of methanol
  2. additionThe mixture was diluted with 10 mL of water
  3. extractionextracted with ethyl acetate (30 mL×3)
  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 (1:10 (v/v) EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-5bc2b4e867ed43eab344e311f465142e
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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