反応 #51583

反応方程式

NaOH

n-hexanoyl chloride

2-mercaptopyridine

→

oil

収率 88.3%

S-2-Pyridyl n-hexanothioate

収率 88.3%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   その他The organic phase was isolated
2. 2
   洗浄washed (water)
3. 3
   乾燥dried (Na2SO4)
4. 4
   濃縮concentrated
5. 5
   その他to afford a yellow oil
6. 6
   workup.DISTILLATIONThe oil was distilled bulb-to-bulb (110-120° C./0.03 mmHg)

実験手順

Following a general procedure (Rao et al., J. Org. Chem. 2000, 65: 1084), to a solution of n-hexanoyl chloride (6.73 g, 50.0 mmol) in CH2Cl2 (200 mL) was added 2-mercaptopyridine (5.55 g, 50.0 mmol) in portions as a solid during 5 min. The resulting mixture was stirred for 1 h, then 2 N NaOH (50 mL) was added. The organic phase was isolated, washed (water), dried (Na2SO4) and concentrated to afford a yellow oil. The oil was distilled bulb-to-bulb (110-120° C./0.03 mmHg) to afford a pale yellow oil (9.24 g, 88%): 1H NMR δ 0.89 (m, 3H), 1.35 (m, 4H), 1.73 (m, 2H), 2.69 (m, 2H), 7.29 (m, 1H), 7.60-7.76 (m, 2H), 8.62 (m, 1H); 13C NMR δ 13.7, 22.1, 24.9, 30.9, 44.0, 123.3, 129.9, 136.9, 150.2, 151.5, 196.4. Anal. Calcd for C11H15NOS: C, 63.12; H, 7.22; N, 6.69. Found: C, 63.02; H, 7.24; N, 6.74.

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