Methanol → HCID 21541519, compound

HRID 1076029Notes

Reaction equation

HRID 1076029 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[O:12][C:13]([CH2:16][CH2:17][C:18]([OH:25])([CH3:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:14][CH:15]=1.CO.C(=O)([O-])[O-].[K+].[K+].O>C(O)(=O)C>[OH:25][C:18]([CH3:24])([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:17][CH2:16][C:13]1[O:12][C:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:26])=[O:2])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 53792507HCID 53792507, compound

Product 1

HCID 21541519HCID 21541519, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of XIII (0.91 g, 0.0025 mole), methanol (10 ml), and 20% potassium cabonate (5 ml) was stirred and refluxed for 90 minutes. The clear yellow solution was mixed with water (15 ml) and acidified to pH 5-6 with acetic acid. The emulsion was extracted with two 15-ml portions of ether. The combined ethereal extracts were dried over magnesium sulfate. Ether was distilled off from a water bath (60°C), at last under 0.1 mm Hg. The yellow, oily residue (0.86 g) was purified by chromatography on three 20 × 20 cm preparative tlc plates (Merck silica gel 60F254 --2 mm layer), and the isolated crude XII herefrom was distilled at 175°-185°C and 0.03 mm Hg to give 0.63 g XII (71%) as a light yellow oil, nD25 1.4844.

Workup

  1. temperaturerefluxed for 90 minutes
  2. extractionThe emulsion was extracted with two 15-ml portions of ether
  3. dry with materialThe combined ethereal extracts were dried over magnesium sulfate
  4. distillationEther was distilled off from a water bath (60°C)
  5. customThe yellow, oily residue (0.86 g) was purified by chromatography on three 20 × 20 cm preparative tlc plates (Merck silica gel 60F254 --2 mm layer)

Sources & evidence

ORD record
ord-f90a37747392403d901cd82cabe48e83
Source dataset
uspto-grants-1976_05
Patent number
US03954813

Reaction notes

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