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

HRID 1684325노트

반응식

HRID 1684325 반응식
[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

참가 물질

4

반응물 2

HCID 73974-Toluenesulfonyl chlorideHCID 867853-Methylcyclopentanol, mixed isomers

생성물 1

HCID 190423383-Methylcyclopentyl 4-methylbenzene-1-sulfonate수율 92.5%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7dac14feabf24f30a2a673feb0a9217c
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05639915

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