Water → HCID 71254072, compound

HRID 1028306Notes

Reaction equation

HRID 1028306 reaction equation
[C:1]1([CH3:13])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1S(Cl)(=O)=O.CCN(CC)CC.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH2:28][CH:29]([OH:32])[CH2:30][OH:31].O>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[C:1]1([CH3:13])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[O:31][CH2:30][CH:29]([OH:32])[CH2:28][O:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 54291342HCID 54291342, compound

Product 1

HCID 71254072HCID 71254072, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

2-Mesitylenesulfonyl chloride (120.8 mg, 0.55 mmol), Bu2SnO (63.1 mg, 0.25 mmol), DMAP (61.9 mg, 0.51 mmol) and Et3N (1 mL) were added to a solution of 3-(pyridin-2-yloxy)propane-1,2-diol (83.7 mg, 0.50 mmol) in toluene (5 mL). The reaction mixture was stirred at room temperature for 2 h. Following the addition of water, the mixture was extracted with CH2Cl2. The organic layers were dried with Na2SO4, and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography to give the title product (123.9 mg, 71%).

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. dry with materialThe organic layers were dried with Na2SO4
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-2eb9ac0be62b4496855bcc495a0275d7
Source dataset
uspto-grants-2014_05
Patent number
US08735440B2

Reaction notes

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