Sodium Hydroxide → 4-(2-Hydroxyethoxy)-2-methoxyphenyl acetate

HRID 1805907

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HRID 1805907 반응식
[C:1](N1C2C(=NC=CC=2)N=N1)(=[O:3])[CH3:2].[OH:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([O:24][CH3:25])[CH:18]=1.[OH-].[Na+]>C1COCC1.Cl>[C:1]([O:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][CH2:14][OH:13])=[CH:18][C:19]=1[O:24][CH3:25])(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 5877724-(2-Hydroxyethoxy)-2-methoxyphenolHCID 7028891-Acetyl-1H-1,2,3-triazolo[4,5-b]pyridine

생성물 1

HCID 673740454-(2-Hydroxyethoxy)-2-methoxyphenyl acetate

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매

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온도
25 °C

실험 절차

A solution of 1-acetyl-1H-1,2,3-triazolo[4,5-b]pyridine (0.248 g, 1.532 mmol) in dry THF (6.13 mL) was added to a solution of 4-(2-hydroxyethoxy)-2-methoxyphenol (0,2821 g, 1.532 mmol) in 1N aq. NaOH (1.532 mL, 1.532 mmol) at 25° C. The reaction was stirred at 25° C. for 3 h. The reaction was diluted with 1IN HCl (20 mL) and extracted with Et2O (3×20 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford the crude product. This was purified by flash chromatography (Biotage Horizon, 25M, Si, ˜20 mL/min, 100% hexanes for 144 mL, gradient to 50% EtOAc in hexanes over 360 mL, gradient to 100% EtOAc over 2034 mL) to afford 4-(2-hydroxyethoxy)-2-methoxyphenyl acetate. Rf=0.28 (50% EtOAc/hexanes). LCMS calc.=249.1; found=249.0 (M+Na)+. 1H NMR (500 MHz, CHCl3): δ 6.87 (d, J=8.7 Hz, 1 H); 6.52 (d, J=2.7 Hz, 1 H); 6.38 (dd, J=8.7, 2.7 Hz, 1 H); 3.96 (t, J=4.7 Hz, 2 H); 3.84 (t, J=4.7 Hz, 2 H); 3.71 (s, 3 H); 2.97 (s, 1 H); 2.24 (s, 3 H).

후처리

  1. extractionextracted with Et2O (3×20 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto afford the crude product
  5. customThis was purified by flash chromatography (Biotage Horizon, 25M, Si, ˜20 mL/min, 100% hexanes for 144 mL, gradient to 50% EtOAc in hexanes over 360 mL, gradient to 100% EtOAc over 2034 mL)

출처 및 근거

ORD 기록
ord-0de759271cde4c73808001985160a88d
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354454B2

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