Sodium Iodide → HCID 19836671, Verbindung

HRID 476885Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 476885
[Si:1]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Si:1]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:22][CH:21]=1)([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 198366434-({[tert-Butyl(diphenyl)silyl]oxy}methyl)phenol

Produkt 1

HCID 19836671HCID 19836671, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Step A ##STR104## A solution of 4-tert-butyldiphenylsilyloxymethylphenol (see Example 1, Step A) (13 g) and ethyl bromoacetate (4.0 ml) in acetone (50 ml) was refluxed for 40 h in the presence of sodium iodide (5.37 g) and potassium carbonate (4.69 g). The reaction mixture was partitioned between ethyl ether and water, and the dried (MgSO4) organic phase was evaporated. Silica gel chromatography of the residue afforded ethyl 2-(4-tert-butyldiphenylsilyloxymethylphenyl)oxyacetate as a colourless syrup (8 g); IR νmax 1735 cm-1 ; NMR (60 MHz, CDCl3)δ 1.1 (9H, s), 1.3 (3H, t, J=6 Hz), 4.2 (2H, q, J=6 Hz), 4.55 and 4.65 (each 2H, s), 6.8-7.8 (10H, m).

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl ether and water
  2. dry with materialthe dried (MgSO4) organic phase
  3. customwas evaporated

Quellen und Nachweise

ORD-Eintrag
ord-b0b2e54ff82c40229a733b8d1d2af9e7
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04886793

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