2,2-Dimethoxypropane → HCID 58560662, compound

HRID 536783Notes

Reaction equation

HRID 536783 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([OH:20])[CH:9]([OH:19])[CH2:10][C:11]#[C:12][C:13]#[C:14][CH:15]([OH:18])[CH:16]=[CH2:17].CO[C:23](OC)([CH3:25])[CH3:24].[CH3:28][C:29]1C=CC(S(O)(=O)=O)=[CH:33][CH:34]=1.O>C1COCC1>[CH2:7]([C@H:8]1[O:20][C:23]([CH3:25])([CH3:24])[O:19][C@@H:9]1[CH2:10][C:11]#[C:12][C:13]#[C:14][C@@H:15]([C:16]1[CH:33]=[CH:34][CH:29]=[CH:28][CH:17]=1)[OH:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 934841-Heptadecene-4,6-diyne-3,9,10-triolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 58560662HCID 58560662, compoundYield 722.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of Panaxytriol derivative (1R,7R,8R)-1-phenyl-2,4-pentadecadiyne-1,7,8-triol (12.8 mg, 39.0 μmol, 1.0 equiv) and 2,2-dimethoxypropane (40.6 mg, 390 μmol, 10 equiv) in dry THF (1.0 mL) was added p-TsOH.H2O (about 1 mg) at 0° C. The cooling bath was removed immediately and the mixture was stirred at room temperature. After 40 min, the reaction was quenched with a saturated solution of NaHCO3 (1 mL). The mixture was extracted with dichloromethane (4 times). The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The crude mixture was purified by gradient flash column chromatography (hexanes/EtOAc=9:18:17:1) to afford the title compound (14.0 mg, 97%) as a pale yellow oil: 1H-NMR (CDCl3, 400 MHz) δ 7.52-7.50 (m, 2H), 7.40-7.32 (m, 3H), 5.50 (s, 1H), 3.83-3.78 (m, 1H), 3.75-3.71 (m, 1H), 2.67-2.56 (m, 2H), 2.30 (br s, 1H), 1.68 (br s, 1H), 1.62-1.26 (m, 12H), 1.40 (s, 6H), 0.88 (t, J=7.0 Hz, 3H); 13C-NMR (CDCl3, 100 MHz) δ 139.75, 128.70, 128.62, 126.62, 108.72, 80.46, 78.11, 77.57, 75.53, 71.35, 66.51, 64.97, 32.90, 31.77, 29.62, 29.13, 27.40, 27.03, 25.94, 23.60, 22.62, 14.07.

Workup

  1. customThe cooling bath was removed immediately
  2. customthe reaction was quenched with a saturated solution of NaHCO3 (1 mL)
  3. extractionThe mixture was extracted with dichloromethane (4 times)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude mixture was purified by gradient flash column chromatography (hexanes/EtOAc=9:18:17:1)

Sources & evidence

ORD record
ord-f35a70eb49f04c5bafb8f456a26ae186
Source dataset
uspto-grants-2014_10
Patent number
US08859615B2

Reaction notes

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