HCID 131715222, compound → HCID 131715223, compound

HRID 1789090Notes

Reaction equation

HRID 1789090 reaction equation
[CH3:1][C:2]([SiH2:5][O:6][CH:7]1[CH2:12][C:11]2([CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[O:10][CH:9]([CH2:18]/[CH:19]=[C:20](\[CH3:26])/[C:21](OCC)=[O:22])[CH2:8]1)([CH3:4])[CH3:3].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.CCOCC>[CH3:4][C:2]([SiH2:5][O:6][CH:7]1[CH2:12][C:11]2([CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[O:10][CH:9]([CH2:18]/[CH:19]=[C:20](\[CH3:26])/[CH:21]=[O:22])[CH2:8]1)([CH3:1])[CH3:3]

Participants

5

Reactant 2

HCID 131715222HCID 131715222, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 131715223HCID 131715223, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 4-[4-[(1,1-dimethylethyl)silyl]oxy-1,7-dioxaspiro[5.5]undec-2-yl]-2-methyl-2E-butenoate, (10.0 g; 27.0 mmoles) in methylene chloride (160 ml) is added finely powdered pyridinium chlorochromate (PCC; 8.7 g; 40.5 mmoles) in a single portion with stirring under nitrogen at 25°. After twenty minutes the reaction mixture is diluted with ether (800 ml) and filtered through celite. The chromium salt residue is washed several times with ether, the washes filtered through celite, and the combined filtrates reduced in volume to 100 ml, filtered through silica gel and concentrated in vacuo to an oil. Chromatography (7.5% ethyl acetate/hexane yields the title compound, 4-[4-[(1,1-dimethylethyl)silyl]oxy-1,7-dioxaspiro[5.5]undec-2-yl]-2-methyl-2E-butenealdehyde; (5.42 g; 54.5%0 as an oil.

Workup

  1. filtrationfiltered through celite
  2. washThe chromium salt residue is washed several times with ether
  3. filtrationthe washes filtered through celite
  4. filtrationfiltered through silica gel
  5. concentrationconcentrated in vacuo to an oil

Sources & evidence

ORD record
ord-97558f66ea4445e291a3e8e538aec74a
Source dataset
uspto-grants-1987_08
Patent number
US04686297

Reaction notes

Loading…