3,4-dihydro-2H-pyran → HCID 21705621, compound

HRID 1596052Notes

Reaction equation

HRID 1596052 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][CH2:14][OH:15].[O:16]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17]1>C(Cl)Cl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][CH2:14][O:15][C:17]1[O:16][CH2:21][CH2:20][CH2:19][CH:18]=1

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 21705612HCID 21705612, compound

Product 1

HCID 21705621HCID 21705621, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 10A (2.96 g, 11.2 mmol) and 3,4-dihydro-2H-pyran (2.04 mL, 22.4 mmol) in CH2Cl2 and was stirred at 0° C. for 10 minutes and at room temperature for 40 minutes. The reaction mixture was partitioned between CH2Cl2 and water, the organic layer dried (Na2SO4), filtered, concentrated, and purified on silica gel with 10% ethyl acetate/hexanes to provide 3.73 g (95%) of the desired compound as an yellow oil.

Workup

  1. customThe reaction mixture was partitioned between CH2Cl2 and water
  2. dry with materialthe organic layer dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on silica gel with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-50037d84bd0e4883aa8eeab3d608a8f0
Source dataset
uspto-grants-2001_09
Patent number
US06288261B1

Reaction notes

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