Water → HCID 89963253, compound

HRID 337880Notes

Reaction equation

HRID 337880 reaction equation
[H-].[Na+].[C@H:3]12[O:9][C@H:8]1[CH2:7][CH2:6][CH2:5][C@H:4]2[OH:10].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH2:19]>C1COCC1>[CH2:11]([O:10][C@:4]1([OH:19])[CH2:5][CH2:6][CH2:7][C@H:8]2[C@H:3]1[O:9]2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 330105AC1L766H

Product 1

HCID 89963253HCID 89963253, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of sodium hydride (63%; 1.20 g, 31.5 mmol) in THF (20 mL), a solution of the (1R*,2R*,6S*)-7-oxabicyclo[4.1.0]heptan-2-ol (3.10 g, 27.2 mmol) prepared in Example 100a in THF (20 mL) was added with cooling on ice, and the mixture was stirred at room temperature for 1 hour. To the reaction solution, benzyl bromide (4.0 mL, 33.4 mmol) was added, and the mixture was stirred at room temperature for 12 hours. To the reaction solution, water (50 mL) was added, followed by extraction with ethyl acetate (50 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=4:1) to yield the title compound (2.85 g, 51%) as a light brown oil.

Workup

  1. temperaturewith cooling on ice
  2. stirringthe mixture was stirred at room temperature for 12 hours
  3. extractionfollowed by extraction with ethyl acetate (50 mL)
  4. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  5. concentrationAfter vacuum concentration
  6. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-16e1b8293e0647809ce88222feb558d7
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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