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

HRID 617077Notes

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.

Sources & evidence

ORD record: ord-9b8f877594ef4113b2256195e29d4e5d
Source dataset: uspto-grants-1978_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04076936

Reaction notes

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