4-Toluenesulfonyl chloride → 3-Methylcyclopentyl 4-methylbenzene-1-sulfonate

HRID 1684325ノート

反応式

HRID 1684325 の反応式
[CH3:1][CH:2]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3]1.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>N1C=CC=CC=1>[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([O:7][CH:4]2[CH2:5][CH2:6][CH:2]([CH3:1])[CH2:3]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 867853-Methylcyclopentanol, mixed isomers

生成物 1

HCID 190423383-Methylcyclopentyl 4-methylbenzene-1-sulfonate収率 92.5%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A round-bottomed flask (100 cc) was charged with 3-methylcyclopentyl alcohol (5.0 g, 49.9 mmol) and p-toluenesulfonyl chloride (10.0 g, 52.5 mmol), followed by the addition of pyridine (50 mL) under ice cooling to form a solution. The solution was stirred for 8 h as it was warmed gradually to room temperature. After completion of the reaction, the reaction mixture was poured into ice water and stirred thoroughly. After extraction with ether (100 mL×2), the organic layers were washed with 2N HCl, water and saturated brine, and dried with anhydrous magnesium sulfate. After the desiccant was removed, the solvent was distilled off under vacuum to give 3-methylcyclopentyl p-toluenesulfonate as a colorless clear oil (11.7 g; yield=92.5%). MP: <30° C. 1H-NMR(CDCl3,TMS,ppm): δ0.93 and 1.00(total 3H, each d,J=6.0Hz), 1.20-2.30(7H,m), 2.48(3H,s), 4.97(1H,m), 7.38(2H,d,J=8.0Hz), 7.85(2H,d,J=8.0Hz).

後処理

  1. customto form a solution
  2. customAfter completion of the reaction
  3. stirringstirred thoroughly
  4. extractionAfter extraction with ether (100 mL×2)
  5. washthe organic layers were washed with 2N HCl, water and saturated brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customAfter the desiccant was removed
  8. distillationthe solvent was distilled off under vacuum

出典と根拠

ORDレコード
ord-7dac14feabf24f30a2a673feb0a9217c
出典データセット
uspto-grants-1997_06
特許番号
US05639915

反応ノート

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