Water → HCID 89525698, compound

HRID 1050982Notes

Reaction equation

HRID 1050982 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[O:8][C:7]([C:9]([C@H:11]2[CH2:15][CH2:14][CH2:13][O:12]2)=[O:10])=[CH:6][CH:5]=1.C(OCC)(=O)C.O>O1CCCC1>[CH3:3][C:4]1[O:8][C:7]([C@@H:9]([CH:11]2[CH2:15][CH2:14][CH2:13][O:12]2)[OH:10])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 89525486HCID 89525486, compound

Product 1

HCID 89525698HCID 89525698, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2.27 g (59.9 mmol; 1.20 eq) of sodium borohydride were added in small portions to a solution of 9.00 g (49.9 mmol; 1.0 eq) of (5-methylfuran-2-yl)-(R)-tetrahydrofuran-2-ylmethanone in 100 ml of tetrahydrofuran cooled to 0° C. The reaction medium was stirred at ambient temperature for 3 hours. The reaction medium was poured into 200 ml of ethyl acetate and then 100 ml of water were added. The aqueous phase was extracted with ethyl acetate and then the organic phases were combined, washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated. 8.10 g de (5-methylfuran-2-yl)-(R)-tetrahydrofuran-2-ylmethanol were obtained. Yield=92%.

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. washwashed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-2df950fd953348f8a9025a74d8ac4451
Source dataset
uspto-grants-2016_07
Patent number
US09388149B2

Reaction notes

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