Pyridine → HCID 13924083, compound

HRID 1789531Notes

Reaction equation

HRID 1789531 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH2:10][CH2:9][CH:8]=[CH:7]1.N1C=CC=CC=1.CS([Cl:21])(=O)=O>CN(C)C=O>[Cl:21][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH2:10][CH2:9][CH:8]=[CH:7]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 15053054HCID 15053054, compound

Product 1

HCID 13924083HCID 13924083, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(4-Hydroxybut-1-yl)cyclopentene {2-cyclopentene-1-butanol} (51 g, 0.37 moles) is diluted in dimethylformamide (100 ml) and added to pyridine (38 g, 0.40 moles). The solution is stirred and methanesulfonyl chloride (46 g, 0.40 moles) is added dropwise over 10 minutes. The reaction is partitioned between hexane (500 ml) and the organic phase separated. The aqueous layer is extracted with hexane (2×500 ml) and the organic extracts combined. The solvent volume is reduced under vacuum and the residue dried over anhydrous magnesium sulfate. The solid is filtered off and the remaining solvent removed leaving a clear yellow oil. The crude product is fractionally distilled under reduced pressure leaving a clear, colorless oil (43 g, 0.27 moles), BP 40°0/0.2 mm.

Workup

  1. customThe reaction is partitioned between hexane (500 ml)
  2. customthe organic phase separated
  3. extractionThe aqueous layer is extracted with hexane (2×500 ml)
  4. dry with materialthe residue dried over anhydrous magnesium sulfate
  5. filtrationThe solid is filtered off
  6. customthe remaining solvent removed
  7. customleaving a clear yellow oil
  8. distillationThe crude product is fractionally distilled under reduced pressure

Sources & evidence

ORD record
ord-4312836202594ea2b2a1aafcadb9333b
Source dataset
uspto-grants-1987_08
Patent number
US04689349

Reaction notes

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