2-Bromopropane → HCID 14423934, compound

HRID 621811Notes

Reaction equation

HRID 621811 reaction equation
C[C:2]([CH3:5])([O-])[CH3:3].[K+].[OH:7][C:8]1[C:12]([OH:13])=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:10][C:9]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].Br[CH:25]([CH3:27])[CH3:26]>CS(C)=O>[CH:2]([O:13][C:12]1[C:8]([O:7][CH:25]([CH3:27])[CH3:26])=[C:9]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[O:10][C:11]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])([CH3:5])[CH3:3]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 234848Diethyl 3,4-dihydroxyfuran-2,5-dicarboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 14423934HCID 14423934, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 1.25 g (11.11 mmol, 1.08 equiv) of potassium tert-butoxide in 7 mL of dimethyl sulfoxide is added rapidly to a room temperature solution of 1.26 g (5.16 mmol) of diethyl 3,4-dihydroxy-2,5-furandicarboxylate (Johnson, T. B. and Johns, C. O., J. Am. Chem. Soc., 28, 489 (1906)) in 10 mL of dimethyl sulfoxide under a nitrogen atmosphere. The resulting solution is stirred at room temperature for 5 minutes and treated with 3.28 g (26.63 mmol, 5.16 equiv) of 2-bromopropane. The resulting reaction mixture is stirred for 24 hours at room temperature under a nitrogen atmosphere and poured onto water. The aqueous mixture is extracted with ethyl acetate (3x). The combined extracts are washed with water (2x) and saturated aqueous sodium chloride, dried over sodium sulfate and concentrated in vacuo to give 1.23 g of diethyl 3,4-diisopropoxy-2,5-furandicarboxylate as a solid.

Workup

  1. customThe resulting reaction mixture
  2. stirringis stirred for 24 hours at room temperature under a nitrogen atmosphere
  3. additionpoured onto water
  4. extractionThe aqueous mixture is extracted with ethyl acetate (3x)
  5. washThe combined extracts are washed with water (2x) and saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a3ddd1969c0405898e896ebab756295
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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