Pyridine → HCID 86748119, compound

HRID 2225858Notes

Reaction equation

HRID 2225858 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][CH2:13][O:14][C:15]1[S:19][C:18]([C:20](=O)[C:21]([OH:23])=[O:22])=[CH:17][CH:16]=1.Cl.[O:26]([NH2:29])[CH2:27][CH3:28].N1C=CC=[CH:32][CH:31]=1>>[CH2:31]([O:23][C:21](=[O:22])/[C:20](=[N:29]/[O:26][CH2:27][CH3:28])/[C:18]1[S:19][C:15]([O:14][CH2:13][CH2:12][O:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[CH:16][CH:17]=1)[CH3:32]

Participants

4

Reactant 3

HCID 1049PyridineHCID 76850O-ethylhydroxylamine hydrochlorideHCID 15234003HCID 15234003, compound

Product 1

HCID 86748119HCID 86748119, compound

Procedure

As described in example 305, 5-[2-(2-naphthalenyloxy)ethoxy]-alpha-oxo-2-thiopheneacetic acid (0.34 g) was combined with ethoxylamine hydrochloride (0.130 g) in pyridine (5 mL) and stirred for 10 days at room temperature. The rnixmre of isomers, obtained after work up of the reaction in the usual manner, were separated by flash chromatography over silica gel (70 g: dichlorornethane-hexane; 4:1 ). Fractions containing the less polar isomer were evaporated to give 0.151 g of (Z)-alpha-(ethoxyimino)-5-[2-(2-naphthalenyloxy)ethoxy]-2-thiopheneacetic acid ethyl ester, mp 114°-115.5° C.

Workup

  1. customThe rnixmre of isomers, obtained after work
  2. customup of the reaction in the usual manner
  3. customwere separated by flash chromatography over silica gel (70 g: dichlorornethane-hexane; 4:1 )
  4. additionFractions containing the less polar isomer
  5. customwere evaporated

Sources & evidence

ORD record
ord-6f85d18b85e74f9f8d5dbad06bb5d8d4
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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