Chloromethyl ethyl ether → 4-(Ethoxymethoxy)-1,1,2,3,3-pentamethyloctahydro-1H-indene

HRID 348508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 348508
[CH3:1][C:2]1([CH3:15])[C:10]2[CH:5]([CH:6]([OH:11])[CH2:7][CH2:8][CH:9]=2)[C:4]([CH3:13])([CH3:12])[CH:3]1[CH3:14].[CH2:16]([O:18][CH2:19]Cl)[CH3:17]>C([N-]C(C)C)(C)C.[Li+]>[CH3:1][C:2]1([CH3:15])[CH:10]2[CH:5]([CH:6]([O:11][CH2:19][O:18][CH2:16][CH3:17])[CH2:7][CH2:8][CH2:9]2)[C:4]([CH3:13])([CH3:12])[CH:3]1[CH3:14]

Komponenten

4

Edukt 2

HCID 18523Chloromethyl ethyl etherHCID 685159571,1,2,3,3-Pentamethyl-tetrahydro-4-indanol

Produkt 1

HCID 210875784-(Ethoxymethoxy)-1,1,2,3,3-pentamethyloctahydro-1H-indeneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2724682Lithium diisopropylamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A reaction flask was charged with 100 mL of lithium diisopropyl amide (LDA, available from Aldrich Chemical Company) (2M in heptane/THF) and cooled to 0° C. 1,1,2,3,3-Pentamethyl-tetrahydro-4-indanol, as described in U.S. Pat. No. 3,636,165, 40 g (0.19 mole) was added in portions to the LDA solution. The reaction was aged 30 minutes then 18.5 g (0.2 mole) of ethoxy methyl chloride was added to the reaction mass at 0° C. The mass was allowed to exotherm to 25° C. The reaction was quenched with 100 g of 10% aqueous sodium carbonate. The mass was transferred to a separatory funnel and water washed. The organic layer was distilled. The procedure afforded a 60% yield (30 g) of 1,1,2,3,3-pentamethyl-hexahydro-4-(ethoxymethoxy)-1H-indene.

Aufarbeitung

  1. customto exotherm to 25° C
  2. customThe reaction was quenched with 100 g of 10% aqueous sodium carbonate
  3. customThe mass was transferred to a separatory funnel
  4. washwater washed
  5. distillationThe organic layer was distilled

Quellen und Nachweise

ORD-Eintrag
ord-e1212bc0e4674c698f0ccf6c99b0ec55
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176324B1

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