4-Toluenesulfonyl chloride → (3,4-dihydro-2H-pyran-2-yl)methyl 4-methylbenzene-1-sulfonate

HRID 905089

反応式

HRID 905089 の反応式
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]=[CH:5][O:4]1.[S:9](Cl)([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10]>N1C=CC=CC=1>[S:9]([O:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]=[CH:5][O:4]1)([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10]

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 955593,4-dihydro-2H-pyran-2-methanol

生成物 1

HCID 13071283(3,4-dihydro-2H-pyran-2-yl)methyl 4-methylbenzene-1-sulfonate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Whilst cooling a solution of 14.2 g of 2-hydroxymethyl-3,4-dihydro-2H-pyran in 120 ml of pyridine on an ice-water bath at 0°-5° C., 28.4 g of crystals of tosyl chloride were added and the mixture was then stirred at room temperature overnight. The salt which precipitated with the aid of a Celite (Trademark) filter aid was separated by filtration and the filtrate was concentrated under reduced pressure. Water was added to the residue and the resulting mixture was extracted with diethyl ether. The ethereal extract was washed with a saturated aqueous solution of sodium bicarbonate and then with aqueous sodium chloride, after which the solvent was evaporated off under reduced pressure. The residue was purified by column chromatography through silica gel eluted with a 7:1 by volume mixture of hexane and ethyl acetate, to give 31.5 g of the title compound, in the form of colourless crystals melting at 47°-48° C.

後処理

  1. customThe salt which precipitated with the aid of a Celite (Trademark)
  2. filtrationfilter aid
  3. customwas separated by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionWater was added to the residue
  6. extractionthe resulting mixture was extracted with diethyl ether
  7. extractionThe ethereal extract
  8. washwas washed with a saturated aqueous solution of sodium bicarbonate
  9. customwith aqueous sodium chloride, after which the solvent was evaporated off under reduced pressure
  10. customThe residue was purified by column chromatography through silica gel
  11. washeluted with a 7:1 by volume mixture of hexane and ethyl acetate

出典と根拠

ORDレコード
ord-3ca6105009eb4bd8a5009d20918adbac
出典データセット
uspto-grants-1983_12
特許番号
US04421758

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