Pyridine → HCID 13341362, compound

HRID 1633405Notes

Reaction equation

HRID 1633405 reaction equation
N1C=CC=CC=1.[CH3:7][C:8]([CH:11]1[CH2:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[O:12]1)(O)[CH3:9].P(Cl)(Cl)(Cl)=O>CCOCC>[C:8](=[C:11]1[CH2:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[O:12]1)([CH3:9])[CH3:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 11286800HCID 11286800, compound

Product 1

HCID 13341362HCID 13341362, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into 40 ml of dried pyridine, was dissolved 6.6 g of 2-(1-methyl-1-hydroxyethyl)-2,3-dihydrobenzofuran. To the solution, with ice-cooling, was added dropwise 11.38 g of phosphorus oxychloride over a period of 10 minutes. After the addition was finished, the mixture was stirred for 2 hours at room temperature and poured into ice water. After ether was added to the mixture, the ether layer was separated and the aqueous layer was extracted twice with 50 ml of ether. The ether layers were combined, washed successively with 5% aqueous hydrochloric acid solution, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain 5.7 g of the crude 2-isopropylidene-2,3-dihydrobenzofuran. This crude product contained 2-isopropylbenzofuran, 2-isopropenyl-2,3-dihydrobenzofuran and small amount of many other unidentifiable impurities, in addition to the intended product. However, because of labileness of the intended product, the crude product was used in the starting material without further purification in the next preparative step.

Workup

  1. temperatureTo the solution, with ice-cooling
  2. additionAfter the addition
  3. customthe ether layer was separated
  4. extractionthe aqueous layer was extracted twice with 50 ml of ether
  5. washwashed successively with 5% aqueous hydrochloric acid solution, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26ea8e785e7e4a5aaea90300e8cd0602
Source dataset
uspto-grants-1984_10
Patent number
US04480118

Reaction notes

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