Hydrochloric Acid → HCID 67433587, compound

HRID 1842840Notes

Reaction equation

HRID 1842840 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@H:16]2[C@H:12]([O:13]C(C)(C)[O:15]2)[C@@H:11]([CH2:19][O:20]C(C)(C)C)[C:10]1=[CH2:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C([O-])(O)=O.[Na+]>CO>[CH2:1]([O:8][C@H:9]1[C:10](=[CH2:25])[C@H:11]([CH2:19][OH:20])[C@H:12]([OH:13])[C@@H:16]1[OH:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 67431947HCID 67431947, compound

Product 1

HCID 67433587HCID 67433587, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 4 (450 mg, 1.3 mmol) was dissolved in MeOH and treated with 3 N HCl at refluxed temperature for 3.5 h. After neutralized with solid NaHCO3, the solvent was removed and the residue was purified by vacuum silica gel column chromatography (MeOH:CH2Cl2=1:30 to 1:10) to give triol 5 (280 mg, 85%) as a white solid. mp 122-124° C.; [α]24D −123.05° (c 0.37, MeOH); 1H NMR (500 MHz, CD3OD) δ 7.46-7.30 (m, 5H), 5.34 (dd, J=1.0 and 3.0 Hz, 1H), 5.21 (s, 1H), 4.77 (d, J=12.0 Hz, 1H), 4.62 (d, J=12.5 Hz, 1H), 4.17-4.14 (m, 2H), 3.95-3.93 (m, 1H), 3.82-3.73 (m, 2H), 2.69-2.66 (m, 1H); 13C NMR (125 MHz, CD3OD) δ 148.9, 138.3, 128.0, 127.6, 127.3, 109.1, 80.8, 71.7, 71.0, 70.8, 61.8, 49.6; HR-MS Calcd. for (C14H18O4+H)+251.1283, found 251.1281.

Workup

  1. temperatureat refluxed temperature for 3.5 h
  2. customthe solvent was removed
  3. customthe residue was purified by vacuum silica gel column chromatography (MeOH:CH2Cl2=1:30 to 1:10)

Sources & evidence

ORD record
ord-398cff8505ba487ea08c48a744a5c1b4
Source dataset
uspto-grants-2015_02
Patent number
US08946244B2

Reaction notes

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