3,4-dihydro-2H-pyran → HCID 12042339, compound

HRID 1377836Notes

Reaction equation

HRID 1377836 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][CH2:6][C@H:7]([OH:20])[CH2:8][CH2:9][C@@H:10]1[C@@H:17]2[C@@H:13]([O:14][C:15](=[O:18])[CH2:16]2)[CH2:12][C@H:11]1[OH:19].[O:24]1[CH:29]=[CH:28][CH2:27][CH2:26][CH2:25]1.O.[C:31]1(C)C=[CH:35][C:34](S(O)(=O)=O)=[CH:33][CH:32]=1.C([O-])(O)=[O:43].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][CH2:6][C@H:7]([O:20][CH:35]1[CH2:34][CH2:33][CH2:32][CH2:31][O:43]1)[CH2:8][CH2:9][C@@H:10]1[C@@H:17]2[C@@H:13]([O:14][C:15](=[O:18])[CH2:16]2)[CH2:12][C@H:11]1[O:19][CH:29]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 12042338HCID 12042338, compound

Product 1

HCID 12042339HCID 12042339, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diol 37 (3.4 g, 10 mmol) and 2.2 g (26 mmol) of 3,4-dihydro-2H-pyran were dissolved in 80 mL of CH2Cl2, and 240 mg (1.3 mmol) of p-toluenesulfonic acid monohydrate was added at 0° C. After 1 h, the reaction was poured into 50 mL of saturated NaHCO3 and the mixture was extracted with CH2Cl2 (3×40 mL). The combined organic layers were dried over MgSO4, filtered, concentrated, and the residue was chromatographed on silica gel (hexane/ethyl acetate, 1/1) to afford 4.5 g (87%) of bis-THP ether 38.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (3×40 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was chromatographed on silica gel (hexane/ethyl acetate, 1/1)

Sources & evidence

ORD record
ord-2a379e1927c44ad9bc4e707730dfd401
Source dataset
uspto-grants-1997_09
Patent number
US05665773

Reaction notes

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