Water → HCID 22640352, compound

HRID 2415114Notes

Reaction equation

HRID 2415114 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([O:16][CH2:17][CH3:18])[CH:15]=1)[O:12][C:11]([CH3:20])([CH3:19])[CH:10]=[C:9]2[C:21]([OH:24])([CH3:23])[CH3:22].O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[CH2:17]([O:16][C:14]1[CH:15]=[C:6]([CH:2]=[O:1])[CH:7]=[C:8]2[C:13]=1[O:12][C:11]([CH3:20])([CH3:19])[CH:10]=[C:9]2[C:21]([OH:24])([CH3:23])[CH3:22])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 22640384HCID 22640384, compound

Product 1

HCID 22640352HCID 22640352, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above prepared 2-(6-[1,3]dioxolan-2-yl-8-ethoxy-2,2-dimethyl-2H-chromen-4-yl)-propan-2-ol was dissolved in 6 ml of methanol and 3 ml of water and treated with 54 mg of pyridinium p-toluenesulfonate. After 15 min. at room temperature, the reaction mixture was poured onto crushed ice/AcOEt, the organic layer washed with water, dried over magnesium sulfate and evaporated to dryness. Flash chromatography (SiO2 with n-hexane/AcOEt=7/3) yielded 194 mg of the title compound as colourless oil.

Workup

  1. additionthe reaction mixture was poured
  2. washthe organic layer washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-8cfef682edb547e7b14ee5a9c7b88276
Source dataset
uspto-grants-2004_11
Patent number
US06818649B2

Reaction notes

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