Methanol → HCID 53984317, compound

HRID 1757074Notes

Reaction equation

HRID 1757074 reaction equation
[C@H:1]1([O:12][CH2:13][C:14]2[CH:15]=[C:16]([C:20]3[CH:21]=[C:22]([CH2:26][C:27]([OH:29])=[O:28])[CH:23]=[CH:24][CH:25]=3)[CH:17]=[CH:18][CH:19]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@@H:2]1[OH:3].[CH3:30]O>S(=O)(=O)(O)O>[C@H:1]1([O:12][CH2:13][C:14]2[CH:15]=[C:16]([C:20]3[CH:21]=[C:22]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH:23]=[CH:24][CH:25]=3)[CH:17]=[CH:18][CH:19]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@@H:2]1[OH:3]

Participants

4

Reactant 2

HCID 887MethanolHCID 10250631HCID 10250631, compound

Product 1

HCID 53984317HCID 53984317, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

3-(3-(α-D-mannopyranosyloxymethyl)phenyl)phenylacetic acid (0.05 g, 0.12 mmol), methanol (10 ml), and concentrated sulfuric acid (2 drops) were heated reflux for 1 hour in a 25 ml flask, then quenched with saturated sodium bicarbonate solution, diluted with water (5 ml), extracted with methylene chloride (3×5 ml), washed with brine (10 ml), dried (MgSO4), concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 5:1/methylene chloride:methanol) which gave methyl 3-(3-(α-D-mannopyranosyloxymethyl)phenyl)phenylacetate (0.04 g, 77%); 1H NMR: (300 MHz, DMSO-d6) 7.2-7.6 (comp, 8H), 4.70 (s, 1H), 4.49-4.80 (comp, 7H), 3.75 (s, 2H), 3.62 (s, 3H), 3.30-3.50 (comp, 5H) ppm; IR: 3383, 1738, 1135, 1066 cm-1.

Workup

  1. temperaturereflux for 1 hour in a 25 ml flask
  2. customquenched with saturated sodium bicarbonate solution
  3. additiondiluted with water (5 ml)
  4. extractionextracted with methylene chloride (3×5 ml)
  5. washwashed with brine (10 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (SiO2, 5:1/methylene chloride:methanol) which

Sources & evidence

ORD record
ord-b963163db7284615b4bd90ebc0216090
Source dataset
uspto-grants-1995_08
Patent number
US05444050

Reaction notes

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