p-Toluenesulfonic acid → HCID 67930799, compound

HRID 728209Notes

Reaction equation

HRID 728209 reaction equation
C1(C)C=CC(S(O)(=O)=[O:8])=CC=1.C(N([CH2:17][CH3:18])CC)C.C[O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27]>>[CH3:27][O:26][C@@H:25]1[CH2:18][C@H:17]([OH:8])[C@H:22]2[CH2:21][O:20][C@@H:24]1[O:23]2

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8150DiglymeHCID 8471Triethylamine

Product 1

HCID 67930799HCID 67930799, compoundYield 57%

Procedure

A solution of this compound (9.6 g) in bis-(2-methoxyethyl) ether (100 ml) containing anhydrous p-toluenesulphonic acid (500 mg) was heated under reflux, while passing a stream of nitrogen through the condenser, for 1 h. The cooled solution was neutralised with triethylamine and evaporated at 50° C. and 1 torr to a dark brown oil. Purification by flash chromatography on silica gel gave the title compound (4.5 g, 57%), identical by melting point, optical rotation, 1H-nmr, and 13C-nmr to the compound described in Preparative Example 1.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customevaporated at 50° C.
  4. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-061ba8dc5f0f42ac83b176bb81b23c84
Source dataset
uspto-grants-1991_09
Patent number
US05047518

Reaction notes

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