3-Furanol, tetrahydro- → HCID 67126717, compound

HRID 574889Notes

Reaction equation

HRID 574889 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.[H-].[Na+].Br[CH2:10][CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1>[CH2:13]([O:12][CH2:11][CH2:10][O:6][CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 99603-Furanol, tetrahydro-HCID 24758Sodium hydrideHCID 73833Benzene, ((2-bromoethoxy)methyl)-

Product 1

HCID 67126717HCID 67126717, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran-3-ol (0.881 g) in tetrahydrofuran (15 mL) was treated with 60% sodium hydride (0.8 g). After 10 minutes, ((2-bromoethoxy)methyl)benzene (3.23 g) was added. The solution was stirred for 16 hours. The reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was separated, and was extracted with additional ethyl acetate twice. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 1:1 ethyl acetate:hexane to provide the title compound.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customThe aqueous layer was separated
  3. extractionwas extracted with additional ethyl acetate twice
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel eluting with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-cdfa0cc165d947eb9b349b33843a8a37
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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