4-Toluenesulfonyl chloride → HCID 20505538, compound

HRID 355267Notes

Reaction equation

HRID 355267 reaction equation
[OH:1][CH:2]([CH2:11][CH3:12])[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>N1C=CC=CC=1>[C:7]([O:6][C:4](=[O:5])[CH2:3][CH:2]([O:1][S:19]([C:16]1[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=1)(=[O:21])=[O:20])[CH2:11][CH3:12])([CH3:8])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 19889219HCID 19889219, compound

Product 1

HCID 20505538HCID 20505538, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of t-butyl 3-hydroxypentanoate (5.22 g, 0.3 mol) in dry pyridine (10 ml) was treated with p-toluenesulfonyl chloride (6.3 g, 0.33 mol) dissolved in dry pyridine (15 ml). The resulting solution was stirred at room temperature for 24 h and poured into ice-water (300 ml). The oily layer was separated and dissolved in ether (140 ml). This solution was washed with water (3×150 ml) and dried over anhydrous MgSO4. Evaporation of the ether under reduced pressure gave an oil (7.75 g, 78.7%). ir (neat) νmax : 1725 (C=O of ester) and 1178 cm-1 (sulfonate); 1Hmr (CDCl3) δ: 0.80 (3H, t), 1.38-1.78 (2H, m), 1.42 (9H, s), 2.32-2.62 (2H, m), 2.38 (3H, s), 4.82 (H, m), 7.25 (2H, d) and 7.70 ppm (2H, d). Anal. calcd for C15H24O5S: C 56.94, H 7.65; found: C 58.39, H 7.54.

Workup

  1. customThe oily layer was separated
  2. dissolutiondissolved in ether (140 ml)
  3. washThis solution was washed with water (3×150 ml)
  4. dry with materialdried over anhydrous MgSO4
  5. customEvaporation of the ether under reduced pressure

Sources & evidence

ORD record
ord-00c411f4f0a44f9c8563e639ce0d5678
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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