Sodium Bicarbonate → HCID 19600257, compound

HRID 1518540Notes

Reaction equation

HRID 1518540 reaction equation
[C:1]([CH2:4][C:5]1[O:6][CH:7]=[CH:8][C:9]=1[CH2:10][C:11](O)=[O:12])(O)=[O:2].B.C1COCC1.C([O-])(O)=O.[Na+]>C1COCC1>[OH:2][CH2:1][CH2:4][C:5]1[O:6][CH:7]=[CH:8][C:9]=1[CH2:10][CH2:11][OH:12]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuranHCID 203250982,3-Di(carboxymethyl)furan

Product 1

HCID 19600257HCID 19600257, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2,3-di(carboxymethyl)furan (35 mmol) in THF (400 mL) is cooled to 0° C. and treated with BH3.THF (174 mmol) over 10 minutes, and stirred for an additional 20 minutes at 0° C. before warming to room temperature overnight. The crude reaction is poured over saturated aqueous NaHCO3 and extracted with ethyl acetate. The organic layer is dried and concentrated to give 2,3-di(2-hydroxyethyl)furan.

Workup

  1. temperaturebefore warming to room temperature overnight
  2. customThe crude reaction
  3. extractionextracted with ethyl acetate
  4. customThe organic layer is dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-31d386794e9e4da28dbe8e449f6fd3db
Source dataset
uspto-grants-2012_07
Patent number
US08232406B2

Reaction notes

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