Triethylamine → HCID 86737907, compound

HRID 893994Notes

Reaction equation

HRID 893994 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][C:17]1([CH3:29])[C@@H:19]([CH:20]=[N:21][O:22][CH2:23][CH:24]=[CH2:25])[C@H:18]1[C:26]([OH:28])=[O:27].C(N(CC)CC)C.[O-][Si]([O-])=O.[Mg+2]>C(OCC)(=O)C.CCOCC.C(Cl)Cl>[CH3:16][C:17]1([CH3:29])[C@@H:19]([CH:20]=[N:21][O:22][CH2:23][CH:24]=[CH2:25])[C@H:18]1[C:26]([O:28][CH2:11][C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:9]=1)=[O:27]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 61680MAGNESIUM SILICATE (synthetic)HCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 53962544HCID 53962544, compound

Product 1

HCID 86737907HCID 86737907, compoundYield 46.9%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3.7 g of 3-phenoxybenzyl bromide and 2.8 g of (1R,cis)-2,2-dimethyl-3-((allyloxyimino)methyl)cyclopropanecarboxylic acid (prepared by a method similar to that shown in Embodiment I) and 1.4 g of triethylamine in 30 ml of ethyl acetate was refluxed for 21/2 hours. The reaction mixture was diluted with ether and washed with water. The ether phase was dried over magnesium sulfate, filtered and stripped to give an oil. This oil in methylene chloride was passed through a florisil column to give 2.5 g of the desired product as an oil [α]D25 +22.9° (CHCl; c=0.012 g/cc).

Workup

  1. temperaturewas refluxed for 21/2 hours
  2. washwashed with water
  3. dry with materialThe ether phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customto give an oil

Sources & evidence

ORD record
ord-2f4754bf36a74072aaad5c8fee0a1a33
Source dataset
uspto-grants-1981_08
Patent number
US04282249

Reaction notes

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