3,4-dihydro-2H-pyran → HCID 86751746, compound

HRID 1940266Notes

Reaction equation

HRID 1940266 reaction equation
[OH:1][CH:2]([CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1)[CH2:3][CH2:4][C:5]1[C:12]2[C:8]([O:9][C:10](=[O:13])[CH:11]=2)=[CH:7][C:6]=1[OH:14].[O:24]1[CH:29]=[CH:28][CH2:27][CH2:26][CH2:25]1.[C:30]([O-:33])(O)=O.[Na+]>C(Cl)Cl>[CH2:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:23][CH:15]1[CH:2]([O:1][CH:4]1[CH2:3][CH2:2][CH2:15][CH2:30][O:33]1)[CH2:3][CH2:4][CH:5]1[CH:12]2[CH:8]([O:9][C:10](=[O:13])[CH2:11]2)[CH2:7][CH:6]1[O:14][CH:29]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 178515354HCID 178515354, compound

Product 1

HCID 86751746HCID 86751746, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 36 from above was dissolved in CH2Cl2 (30 mL) and the mixture was cooled to 0° C. 3,4-dihydro-2H-pyran was added (0.42 g, 5.0 mmol), followed by P-toluenesulfonic acid monohydrate (50 mg, 0.2 mmol). The solution was stirred at room temperature for 2 h, poured into saturated aqueous NaHCO3, and extracted with CH2Cl2. The solution was dried over MgSO4, filtered, and concentrated, and the residue was chromatographed on silica gel to afford 0.4 g (36%) of 37 as a viscous oil. 1H NMR (CDCl3) δ 7.2 (m, 4 H), 5.0 (m, 1 H), 4.7 (m, 2 H).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-4e4b1ca5eea0452980418e399a7dfe01
Source dataset
uspto-grants-1997_12
Patent number
US05698733

Reaction notes

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