4-Toluenesulfonyl chloride → HCID 13189250, compound

HRID 905014Notes

Reaction equation

HRID 905014 reaction equation
[CH2:1]([O:3][CH:4]([O:6][C:7]([CH3:15])([CH3:14])[C:8]([F:13])([F:12])[CH2:9][CH2:10][OH:11])[CH3:5])[CH3:2].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>N1C=CC=CC=1>[CH3:26][C:16]1[CH:21]=[CH:20][C:19]([S:22]([O:11][CH2:10][CH2:9][C:8]([F:12])([F:13])[C:7]([O:6][CH:4]([O:3][CH2:1][CH3:2])[CH3:5])([CH3:15])[CH3:14])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 131892494-(1-Ethoxyethoxy)-3,3-difluoro-4-methylpentan-1-ol

Product 1

HCID 13189250HCID 13189250, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1.00 g (0.0044 mol) of 4-(1-ethoxyethoxy)-3,3-difluoro-4-methyl-1-pentanol, 4 mL of pyridine and 1.27 g (0.0066 mol) of p-toluenesulfonyl chloride was stirred at 0° C. for 18 hr. The mixture was quenched with ice chips. The mixture was then poured into water and extracted with methylene chloride. The organic phase was sequentially washed with 10% aqueous sulfuric acid and saturated aqueous sodium bicarbonate solution. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated to dryness to yield oily 4-(1-ethoxyethoxy)-3,3-difluoro-4-methyl-1-pentanol 1-(4-methylbenzenesulfonate). NMR (CDCl3) δ4.93 (quartet, 1, J=7 Hz), 4.27 (triplet, 2, J=7 Hz), 3.45 (quartet, 2, J=7 Hz), 2.45 (singlet, 3), 2.36 (multiplet, 2), 1.27 (triplet, 6, J=1 Hz), 1.24 (doublet, 3 J=7 Hz), and 1.15 ppm (triplet, 3, J=7 Hz).

Workup

  1. customThe mixture was quenched with ice chips
  2. additionThe mixture was then poured into water
  3. extractionextracted with methylene chloride
  4. washThe organic phase was sequentially washed with 10% aqueous sulfuric acid and saturated aqueous sodium bicarbonate solution
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-6b61fc97dba0463bb493461cb9053360
Source dataset
uspto-grants-1983_12
Patent number
US04421690

Reaction notes

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