Benzylhydroxylamine → N-(2-methyl-3-tetrahydropyranyloxypropylidene)-benzylamine-N-oxide

HRID 329792Notes

Reaction equation

HRID 329792 reaction equation
[CH3:1][CH:2]([CH2:5][O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)[CH:3]=O.[CH2:13]([NH:20][OH:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[Ca+2].[Cl-]>CCOCC>[CH3:1][CH:2]([CH2:5][O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)[CH:3]=[N+:20]([O-:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 2794173BenzylhydroxylamineHCID 5284359Calcium ChlorideHCID 108883772-Methyl-3-tetrahydropyranyloxypropanal

Product 1

HCID 86743656N-(2-methyl-3-tetrahydropyranyloxypropylidene)-benzylamine-N-oxideYield 62.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

An etheral solution (1 ml) of 2-methyl-3-tetrahydropyranyloxypropanal (37.9 mg; 0.20 mmol) was added dropwise to a suspension of benzylhydroxylamine (28.7 mg; 0.23 mmol) and powdery calcium chloride (22.2 mg; 0.20 mmol) in ether (0.5 ml) at 0° C., and the resultant mixture was stirred for 1.5 hours. The reaction mixture was purified by TLC using ethyl acetate to give N-(2-methyl-3-tetrahydropyranyloxypropylidene)-benzylamine-N-oxide (34.9 mg; yield, 57%).

Workup

  1. customThe reaction mixture was purified by TLC

Sources & evidence

ORD record
ord-68d277b2cc2e4d4398f4f42e20a20de1
Source dataset
uspto-grants-1990_01
Patent number
US04892961

Reaction notes

Loading…