Water → cis-1-(tert-Butyldimethylsilyloxymethyl)-4-(2-tridecenyloxymethyl)benzene

HRID 2255021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2255021
[H-].[Na+].[CH2:3]([OH:16])/[CH:4]=[CH:5]\[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[Si:17]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32]I)=[CH:28][CH:27]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].O>C1COCC1.CCOCC>[Si:17]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:32][O:16][CH2:3]/[CH:4]=[CH:5]\[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:30][CH:31]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:19]

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5364998(Z)-2-Tridecen-1-olHCID 107373351-[(tert-Butyldimethylsilyl)oxymethyl]-4-iodomethylbenzene

Produkt 1

HCID 10526760cis-1-(tert-Butyldimethylsilyloxymethyl)-4-(2-tridecenyloxymethyl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A flask was charged with 60 mg of a 60% dispersion of NaH in oil. The dispersion was washed with three 2-mL portions of THF. The NaH was suspended in 5 mL of THF and cooled to 0° C. A solution Of cis-2-tridecen-1-ol (206 mg, 1.1 mmol, 1.1 equiv) in THF (1 mL) was slowly added to the mixture. After 25 minutes the cold bath was removed and stirring was continued for an additional 10 minutes. At this time a solution of (40) (361 mg, 1 mmol) in THF (1 mL) was added and stirring was continued for 12 hours. The mixture was poured into water (20 mL) and ether (25 mL). The organic layer was separated and washed with three 10-mL portions of water. The ether extract was dried (MgSO4) filtered and concentrated by rotary evaporation to yield a yellow oil. Purification by flash silica gel chromatography (95:05 petroleum ether/EtOAc) afforded 341 mg (85%) of the coupled produced (41) as a clear colorless oil: Rf 0.80 (9:1 petroleum ether/EtOAc); 1H NMR (CDCl3) δ 7.20 (s, 4 H), 5.61 (m, 2H), 4.76 (s, 2H), 4.52 (s, 2H), 4.08 (d, J=4.8 Hz, 2H), 2.05 (m, 2H), 1.29 (m, 16 H), 0.97 (s, 9 H), 0.91 (t, J=6.9 Hz, 3 H), 0.12 (s, 6 H); 13C NMR (CDCl3) δ 140.76, 137.04, 127.71, 126.04, 125.98, 71.86, 65.58, 64.80, 31.92, 29.62, 29.56, 29.52, 29.24, 29.36, 27.61, 25.94, 22.69, 18.57, 14.12, -5.25. ##STR8##

Aufarbeitung

  1. washThe dispersion was washed with three 2-mL portions of THF
  2. customAfter 25 minutes the cold bath was removed
  3. stirringstirring
  4. waitwas continued for 12 hours
  5. customThe organic layer was separated
  6. washwashed with three 10-mL portions of water
  7. extractionThe ether extract
  8. dry with materialwas dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated by rotary evaporation
  11. customto yield a yellow oil
  12. customPurification by flash silica gel chromatography (95:05 petroleum ether/EtOAc)
  13. customafforded 341 mg (85%) of the

Quellen und Nachweise

ORD-Eintrag
ord-deb653a5f1cb4fdb859be4361c103537
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05238832

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