1,4-Dioxane--water (1/1) → HCID 67851959, compound

HRID 486815Notes

Reaction equation

HRID 486815 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:20])[CH:6]=[C:7]([S:14][CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[C:8]2=[O:13].O.[O:22]1CCOCC1>O>[OH:22][CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:20])[CH:6]=[C:7]([S:14][CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[C:8]2=[O:13]

Participants

4

Reactant 2

HCID 218864351,4-Dioxane--water (1/1)HCID 131718346HCID 131718346, compound

Product 1

HCID 67851959HCID 67851959, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The bromomethyl acid 1b (6 mmol) is mixed in 50 mL of water-dioxane (3:2, v/v) and refluxed with stirring for 1 hour. The solution is then diluted with water (300 mL) and extracted with CHCl3 (3×300 mL). The CHCl3 solution is dried (Na2SO4), concentrated, and chromatographed on a silica gel column (CHCl3 -EtOAc, 7:3 v/v) to yield (5-hydroxymethyl-1,4-naphthoquinonyl thio)-propionic acid, designated 1d.

Workup

  1. temperaturev/v) and refluxed
  2. extractionextracted with CHCl3 (3×300 mL)
  3. dry with materialThe CHCl3 solution is dried (Na2SO4)
  4. concentrationconcentrated
  5. customchromatographed on a silica gel column (CHCl3 -EtOAc, 7:3 v/v)

Sources & evidence

ORD record
ord-4c2ea42023e84c1ba1eb154d44e921b6
Source dataset
uspto-grants-1994_03
Patent number
US05292873

Reaction notes

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