Water → HCID 53853952, compound

HRID 2255151Notes

Reaction equation

HRID 2255151 reaction equation
[CH2:1]([O:4][CH2:5][C:6]1[C:7]([Cl:25])=[N+:8]([O-:24])[C:9]([CH2:20][CH:21]([CH3:23])[CH3:22])=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]=1)[CH:2]=[CH2:3].C(N(C(C)C)CC)(C)C.O>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh].C(O)C>[CH:1]([O:4][CH2:5][C:6]1[C:7]([Cl:25])=[N+:8]([O-:24])[C:9]([CH2:20][CH:21]([CH3:22])[CH3:23])=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]=1)=[CH:2][CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 81531DiisopropylethylamineHCID 19739768HCID 19739768, compound

Product 1

HCID 53853952HCID 53853952, compoundYield 130%

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 702EthanolSolvent

Procedure

To 200 mg of 3-allyloxymethyl-5-benzyloxy-2-chloro-6-isobutylpyrazine 1-oxide were added 195 μl of diisopropylethylamine, 51 mg of a Wilkinson's catalyst ##STR69## and 4 ml of water (10% volume)-ethanol. The mixture was reacted for 3 hours at 85°-90° C. The catalyst was removed by filtration to obtain 260 mg of 3-(1-propenyl)oxymethyl-5-benzyloxy-2-chloro-6-isobutylpyrazine 1-oxide (Compound B-6) [a cis/trans (about 4/3) mixture] as a colorless oily substance.

Workup

  1. customThe mixture was reacted for 3 hours at 85°-90° C
  2. customThe catalyst was removed by filtration

Sources & evidence

ORD record
ord-a38aed4ca8f64a11bc212e68fca3eb39
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

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