Hydrochloric Acid → (2,5-Dimethylfuran-3-yl)methanol

HRID 1877044

Reaction equation

HRID 1877044 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH3:10])=[CH:5][C:6]=1[C:7](Cl)=[O:8].[BH4-].[Na+].Cl.O>O1CCCC1>[CH3:1][C:2]1[O:3][C:4]([CH3:10])=[CH:5][C:6]=1[CH2:7][OH:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 27348042,5-Dimethyl-3-furoyl ChlorideHCID 4311764Sodium borohydride

Product 1

HCID 10396847(2,5-Dimethylfuran-3-yl)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2,5-dimethylfuran-3-carbonyl chloride (5.0 g) in tetrahydrofuran (20 mL) was added dropwise to a suspension of sodium borohydride (3.4 g) in tetrahydrofuran (50 mL) at 0° C. and, after the completion of the dropwise addition, the mixture was stirred at 0° C. for 1 hr. The reaction mixture was treated with 1N hydrochloric acid, poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (3.8 g, 100%) as an oil.

Workup

  1. additionafter the completion of the dropwise addition
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ec82b427591b410b992cbafd1a71bb53
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Linked notes

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