Water → HCID 89525504, compound

HRID 1050971Notes

Reaction equation

HRID 1050971 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[O:8][C:7]([C:9]([CH:11]2[CH2:15][CH2:14][CH2:13][S:12]2)=[O:10])=[CH:6][CH:5]=1.C(OCC)(=O)C.O>O1CCCC1.CO>[CH3:3][C:4]1[O:8][C:7]([CH:9]([CH:11]2[CH2:15][CH2:14][CH2:13][S:12]2)[OH:10])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 64166051HCID 64166051, compound

Product 1

HCID 89525504HCID 89525504, compoundYield 101.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

6.69 g (0.18 mol; 1.20 eq) of sodium borohydride were added in small portions to a solution of 30.24 g (0.15 mol; 1.0 eq) of (5-methylfuran-2-yl)-(tetrahydrothiophen-2-yl)methanone in 300 ml of tetrahydrofuran and 50 ml of methanol cooled to 0° C. The reaction medium was stirred at ambient temperature for 3 hours. The reaction medium was poured into 400 ml of ethyl acetate and then 200 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. 30.22 g of (5-methylfuran-2-yl)-(tetrahydrothiophen-2-yl)methanol were obtained. Quantitative yield.

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-910fa3ce948a4aab940d8e76049c195a
Source dataset
uspto-grants-2016_07
Patent number
US09388149B2

Reaction notes

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