Trityl chloride → Triethylammonium 2-triphenylmethoxyimino-2-(fur-2-yl) acetate

Reaction equation

[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[C:8]1([C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)Cl)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH:28][N:29]=[C:30]([C:34]1[O:35][CH:36]=[CH:37][CH:38]=1)[C:31]([OH:33])=[O:32]>>[C:8]1([C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:28][N:29]=[C:30]([C:34]2[O:35][CH:36]=[CH:37][CH:38]=2)[C:31]([O-:33])=[O:32])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:1]([NH+:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2]

Participants

Reactant 3

HCID 6456Trityl chloride

HCID 8471Triethylamine

HCID 727327832-(Fur-2-yl)-2-hydroxyiminoacetic acid

Product 1

HCID 86734467Triethylammonium 2-triphenylmethoxyimino-2-(fur-2-yl) acetateYield 79%

Procedure

Triethylamine (35 ml, 250 mmole), triphenylchloromethane (35 g, 125 mmole) and 2-hydroxyimino-2-(fur-2-yl)-acetic acid (syn isomer) 15.505 g, 100 mmole) were reacted together essentially as described in Preparation 2(a) to give triethylammonium 2-triphenylmethoxyimino-2-(fur-2-yl) acetate (syn isomer) as a pale-yellow solid (39.5 g, 79 mmole, 79%), m.p. 170° to 172° (dec), λmax 275.5 nm, inflexions at 265 and 271.5 nm (ε 17,900; 15,900 and 17,500 respectively). (b) The title compound was prepared from the product of (a) above essentially as described in Preparation 2(b) and used without further purification in Example 2.