3,4-dihydro-2H-pyran → HCID 66779971, compound

HRID 1907316Notes

Reaction equation

HRID 1907316 reaction equation
[O:1]([CH2:9][CH:10]1[CH2:13][CH:12]([OH:14])[CH2:11]1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1>ClCCl.C1(C)C(S(O)(=O)=O)=CC=CC=1>[C:5]([Si:2]([CH3:4])([CH3:3])[O:1][CH2:9][CH:10]1[CH2:11][CH:12]([O:14][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][O:15]2)[CH2:13]1)([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 534160013-(((Tert-butyldimethylsilyl)oxy)methyl)cyclobutan-1-ol

Product 1

HCID 66779971HCID 66779971, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 69252-Methylbenzenesulfonic acidCatalystHCID 6344DichloromethaneSolvent2×

Procedure

3-(tert-Butyl dimethylsilanoxymethyl)-cyclobutanol (1.46 g) in dry dichloromethane was treated with dihydropyran (1.7 g) and toluenesulphonic acid (0.01 g) for 3 hours. The reaction mixture was diluted with dichloromethane, the organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate in cyclohexane (0 to 1:9 by volume) to give the title compound (1.62 g).

Workup

  1. washthe organic extracts were washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluting with ethyl acetate in cyclohexane (0 to 1:9 by volume)

Sources & evidence

ORD record
ord-69929dda220942439770d636c2b338c6
Source dataset
uspto-grants-2013_12
Patent number
US08598154B2

Reaction notes

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