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2-Chlormethyl-8-(1,1-dimethylethyl)-1,4-dioxaspiro(4.5)decan → 8-t-Butyl-2-(phthalimidomethyl)-1,4-dioxaspiro(4,5)decane

HRID 2211123
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2211123
[C:1]([CH:5]1[CH2:16][CH2:15][C:8]2([O:12][CH:11]([CH2:13]Cl)[CH2:10][O:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[K]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[C:1]([CH:5]1[CH2:16][CH2:15][C:8]2([O:12][CH:11]([CH2:13][N:21]3[C:20](=[O:22])[C:19]4=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]4[C:17]3=[O:27])[CH2:10][O:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]
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Komponenten

5

Edukt 2

HCID 143262942-Chlormethyl-8-(1,1-dimethylethyl)-1,4-dioxaspiro(4.5)decanHCID 24194345Phthalimide potassium salt2×

Produkt 1

HCID 199636648-t-Butyl-2-(phthalimidomethyl)-1,4-dioxaspiro(4,5)decaneAusbeute 101,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysator
HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

A mixture of 8-t-butyl-2-chloromethyl-1,4-dioxaspiro(4,5)decane (10 g, 40 mmol) (prepared as described in EP 281842; see also the references cited in this document for related compounds), potassium phthalimide (8.9 g, 48 mmol) and a catalytic amount of tetra-n-butyl ammonium iodide in DMF (80 ml) were heated to 120° C. for 3 hours. Additional potassium phthalimide (2.8 g, 16 mmol) was then added and heating was continued for 6 hours. The solvent was then evaporated in vacuo and toluene (150 ml) was added. After filtration from insoluble material the organic phase was washed two times with brine (100 ml), dried (MgSO4) and evaporated in vacuo. The resulting residue (22 g) was purified by flash chromatography on silica (toluene/ethylacetate 3:1) yielding the title compound as light yellow crystals (14.5 g, Fp. 97°-115° C.).

Aufarbeitung

  1. customprepared
  2. temperatureheating
  3. customThe solvent was then evaporated in vacuo and toluene (150 ml)
  4. additionwas added
  5. filtrationAfter filtration from insoluble material the organic phase
  6. washwas washed two times with brine (100 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo
  9. customThe resulting residue (22 g) was purified by flash chromatography on silica (toluene/ethylacetate 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-31dc803d952046ef8cf7242cdcb9b10a
Quelldatensatz
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05462944

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