Water → HCID 86737698, compound

HRID 905253Notes

Reaction equation

HRID 905253 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.[C:16]([C:18]([C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1)=[CH:19][CH:20]1[CH:22]([C:23]([OH:25])=[O:24])[C:21]1([CH3:27])[CH3:26])#[N:17].C(N(CC)CC)C.O>CN(C)C=O>[C:16]([C:18]([C:28]1[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=1)=[CH:19][C@H:20]1[C@H:22]([C:23]([O:25][CH2:11][C:10]2[CH:13]=[CH:14][CH:15]=[C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:9]=2)=[O:24])[C:21]1([CH3:27])[CH3:26])#[N:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 70528624HCID 70528624, compound

Product 1

HCID 86737698HCID 86737698, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

m-Phenoxybenzylbromide (3.68 g; 0.014 mole) is added to a solution of 3-(β-cyano-p-methylstyryl)-2,2-dimethylcyclopropanecarboxylic acid (3.19 g; 0.0125 mole) and triethylamine (1.27 g; 0.0125 mole) in dry dimethylformamide and the reaction mixture stirred for 18 hours at room temperature. The reaction mixture, containing some precipitated salts, is poured into water and extracted with ether (2×75 ml). The combined ether extracts are washed several times with water, then with sodium bicarbonate solution and saturated sodium chloride solution. Evaporation of the ether solution yields 3.42 g (62.5%) of a yellow oil. Purification of this yellow oil by dry column chromatography (silica gel; eluent: 1:1 methylene chloride:hexane) affords 0.96 g of the trans isomer and 0.6 g of the cis isomer.

Workup

  1. additionThe reaction mixture, containing some precipitated salts
  2. extractionextracted with ether (2×75 ml)
  3. washThe combined ether extracts are washed several times with water
  4. customEvaporation of the ether solution

Sources & evidence

ORD record
ord-434718fd53954e43b1ca2a35b2fb55f0
Source dataset
uspto-grants-1983_12
Patent number
US04423062

Reaction notes

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