HCID 20157963, compound → HCID 20157956, compound

HRID 986560Notes

Reaction equation

HRID 986560 reaction equation
Br[CH:2]([C:11]1[CH:25]=[CH:24][CH:23]=[CH:22][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:3](Br)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].CC(C)([O-])C.[K+]>CS(C)=O>[C:2]([C:11]1[CH:25]=[CH:24][CH:23]=[CH:22][C:12]=1[O:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 20157963HCID 20157963, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20157956HCID 20157956, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of ethyl 4-[2-(1,2-dibromooctyl)-phenoxy]butanoate, (2.01 g, 4.20 mmole), potassium t-butoxide, (1.33 g, 11.1 mmole) and 18 crown6 (5 mg) in dry dimethylsulphoxide (25 ml) was stirred at ambient temperature for 4 h, then at 100° C. for 15 h. The reaction was evaporated in vacuo to a low volume, poured into saturated brine and acidified with dilute hydrochloric acid. The product was extracted with ethyl acetate (three times) and the combined organic phases washed with water (three times), and dried, (MgSO4). Evaporation in vacuo yielded the crude product as a pale brown oil, which was purified by column chromatography using silica gel and eluting with dichloromethane/petroleum ether 60°-80° C., (1:1). The intermediate bromoalkane was collected first, followed by 0.380 g (29%) of the acetylene as a colourless oil.

Workup

  1. customThe reaction was evaporated in vacuo to a low volume
  2. additionpoured into saturated brine
  3. extractionThe product was extracted with ethyl acetate (three times)
  4. washthe combined organic phases washed with water (three times)
  5. customdried
  6. customEvaporation in vacuo

Sources & evidence

ORD record
ord-1916c8d301c3483a9746696f98a75d4e
Source dataset
uspto-grants-1987_12
Patent number
US04713486

Reaction notes

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