Sodium Hydroxide → HCID 19879323, compound

HRID 1885577Notes

Reaction equation

HRID 1885577 reaction equation
[OH-].[Na+].Br[CH:4]([CH:7]([C:9]1[CH:13]=[CH:12][S:11][CH:10]=1)[OH:8])[CH2:5][OH:6]>O.C(O)C>[O:8]1[CH:7]([C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[CH:4]1[CH2:5][OH:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19879314HCID 19879314, compound

Product 1

HCID 19879323HCID 19879323, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

0.8 g of sodium hydroxide in 15 ml of water is added to a solution of 2.4 g of (2RS,3SR)-2-bromo-3-(thiophen-3-yl)-propane-1,3-diol in 25 ml of ethanol. The reaction mixture is stirred for 40 minutes at room temperature, the ethanol is evaporated off in vacuo and the residue is diluted with 400 ml of water. Extraction is carried out with dichloromethane (3×100 ml), the extracts are dried over sodium sulfate and the solvent is evaporated off. The residue is chromatographed on silica gel with dichloromethane/acetone (9:1). The title compound is obtained in the form of light-yellow crystals, m.p.=63°-65° C.

Workup

  1. customthe ethanol is evaporated off in vacuo
  2. additionthe residue is diluted with 400 ml of water
  3. extractionExtraction
  4. dry with materialthe extracts are dried over sodium sulfate
  5. customthe solvent is evaporated off
  6. customThe residue is chromatographed on silica gel with dichloromethane/acetone (9:1)

Sources & evidence

ORD record
ord-a3d42c43b47f4565a57ad17b18438608
Source dataset
uspto-grants-1992_09
Patent number
US05145868

Reaction notes

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