Pyridine → HCID 88522902, compound

HRID 1723041Notes

Reaction equation

HRID 1723041 reaction equation
[C:1]([O:9][CH2:10][C:11]1([CH2:16][O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][CH:12]1[CH2:14][OH:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.N1C=CC=C[CH:38]=1>C1CCCCC1.C(OCC)(=O)C>[C:18]([O:17][CH2:16][C:11]1([CH2:10][O:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][CH:12]1[CH2:14][O:15][S:33]([C:30]1[C:31]([CH3:38])=[CH:32][CH:27]=[CH:28][CH:29]=1)(=[O:34])=[O:35])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 14236874HCID 14236874, compound

Product 1

HCID 88522902HCID 88522902, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 21867204Cyclohexane ethylacetateSolvent

Procedure

A solution of 4.5 g (13.2 mmole) of 1,1-bis(benzoyloxymethyl)-2-hydroxymethylcyclopropane in 50 ml of dry pyridine was treated with 7 g (37 mmoles) of p-tosyl chloride and stirred at 22° for 1.5 hours. TLC in cyclohexane-ethyl acetate (2:1) (Rf 0.6) indicated that the reaction was complete. The reaction was concentrated and the residue was dissolved in 150 ml of EtOAc and washed with 50 ml of water, 100 ml saturated NaHCO3, four 250 ml portions of water and 50 ml of saturated NaCl. The ethyl acetate layer was dried (MgSO4), filtered and concentrated to 9 g of residual solid. The crude product was chromatographed on 500 ml of silica gel in cyclohexane-ethyl acetate (5:1). Fractions containing only product were combined and concentrated to give 3.36 g (54%) of the title compound.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue was dissolved in 150 ml of EtOAc
  3. washwashed with 50 ml of water, 100 ml saturated NaHCO3, four 250 ml portions of water and 50 ml of saturated NaCl
  4. dry with materialThe ethyl acetate layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to 9 g of residual solid
  7. customThe crude product was chromatographed on 500 ml of silica gel in cyclohexane-ethyl acetate (5:1)
  8. additionFractions containing only product
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-773204a63e7f4131886100948d3e5443
Source dataset
uspto-grants-1989_08
Patent number
US04859680

Reaction notes

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