Water → HCID 24804128, compound

HRID 2383978Notes

Reaction equation

HRID 2383978 reaction equation
Cl[C:2]1(C(O)=O)[C:4]2([CH2:9][CH2:8][C:7]([C:25]#[N:26])([C:10]3[C:18]4[C:17]5[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=5[O:15][C:14]=4[C:13]([O:23][CH3:24])=[CH:12][CH:11]=3)[CH2:6][CH2:5]2)[O:3]1.[OH2:30]>CS(C)=O>[C:25]([C:7]1([C:10]2[C:18]3[C:17]4[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=4[O:15][C:14]=3[C:13]([O:23][CH3:24])=[CH:12][CH:11]=2)[CH2:8][CH2:9][CH:4]([C:2]([OH:3])=[O:30])[CH2:5][CH2:6]1)#[N:26]

Participants

4

Reactant 2

HCID 962WaterHCID 86635827HCID 86635827, compound

Product 1

HCID 24804128HCID 24804128, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

At room temperature, to a solution of the epoxy acid (0.380 g, 0.0009 mol) (as formed in step 2) in DMSO (8 ml)/Water (0.8 ml) sodium chloride (0.055 g, 0.000.9 mol) was charged and the reaction mass was heated to 100° C. for 7 hrs. Once the product has formed, the reaction mass was quenched with water and extracted with ethyl acetate. The organic layer was dried with sodium sulfate and concentrated under vacuum. 4-cyano-4-(4-methoxy-dibenzofuran-1-yl)-cyclohexane carboxylic acid was isolated by column chromatography. Yield 0.035 g, (10.8%)

Workup

  1. customOnce the product has formed
  2. customthe reaction mass was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-338f62e7cd274a798bcafb96b635f352
Source dataset
uspto-grants-2012_09
Patent number
US08263648B2

Reaction notes

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