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Pyridine → HCID 88522902, compound

HRID 2290542
Notes
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Reaction equation

HRID 2290542 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-2cd0d7e26e724996b6a9cfdd0e79856b
Source dataset
uspto-grants-1986_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04617304

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes