p-Toluenesulfonic acid → HCID 86753106, compound

HRID 2393576Notes

Reaction equation

HRID 2393576 reaction equation
[CH:1]1([C@@H:7]([OH:20])[CH2:8][CH2:9][C@@H:10]2[C@@H:17]3[C@@H:13]([O:14][C:15](=[O:18])[CH2:16]3)[CH2:12][C@H:11]2[OH:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:21]1[CH2:26][O:25][CH:24]=[CH:23][CH2:22]1.ClCl.[CH3:29][C:30]1C=C[C:33](S(O)(=O)=O)=[CH:34][CH:35]=1.C([O-])(O)=[O:41].[Na+]>>[CH:1]1([C@@H:7]([O:20][CH:33]2[CH2:34][CH2:35][CH2:30][CH2:29][O:41]2)[CH2:8][CH2:9][C@@H:10]2[C@@H:17]3[C@@H:13]([O:14][C:15](=[O:18])[CH2:16]3)[CH2:12][C@H:11]2[O:19][CH:24]2[CH2:23][CH2:22][CH2:21][CH2:26][O:25]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 24526ChlorineHCID 516892Sodium BicarbonateHCID 86753105HCID 86753105, compound

Product 1

HCID 86753106HCID 86753106, compoundYield 89%

Procedure

To a mixture of 44 (3.7 g, 12.9 mmol), DHP (2.9 g, 35 mmol), and CH2 Cl2 (80 mL) at 0° C. was added pTSA (300 mg, 1.58 mmol). After 30 min 50 mL of saturated NaHCO3 was added, the layers were separated, the aqueous layer was extracted with CH2CL2 (2×50 mL), the combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was chromatographed on silica gel (1/1 hexane/ethyl acetate) to afford bis-THP ether 45 (4.89 g, 89%).

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with CH2CL2 (2×50 mL)
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was chromatographed on silica gel (1/1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-80cec380e1bf47768a0300af920fc13b
Source dataset
uspto-grants-1998_09
Patent number
US05807892

Reaction notes

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