3,4-dihydro-2H-pyran → 3-(Tetrahydro-pyran-2-yloxymethyl)-benzonitrile

HRID 585540노트

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HRID 585540 반응식
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1>C(Cl)Cl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7]

참가 물질

5

반응물 2

HCID 80803,4-dihydro-2H-pyranHCID 27346773-(Hydroxymethyl)benzonitrile

생성물 1

HCID 219279093-(Tetrahydro-pyran-2-yloxymethyl)-benzonitrile수율 89.9%

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 6344Dichloromethane용매2회

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온도
25 °C

실험 절차

3-(Hydroxymethyl)benzonitrile (5.00 g; 37.6 mmoles) and 3,4-Dihydro-2H-pyran (3.77 mL; 41.4 mmoles) were dissolved in methylene chloride (25 mL) under nitrogen and the solution was cooled to 5° C. p-Toluenesulfonic acid monohydrate (74 mg; 0.37 mmoles) was added and the mixture was stirred for 2 hours at 25° C. The reaction mixture was diluted with methylene chloride (25 mL). The solution was washed with aqueous sodium bicarbonate solution (30 mL) and aqueous sodium chloride solution (30 mL). The solution was dried over sodium sulfate and filtered. The solvent was removed under vacuum to give the product, 3-[(tetrahydro-2H-pyran-2-yloxy)methyl]benzo-nitrile (7.34 g; 89%) as an oil. 1H NMR (400 MHz) CDCl3 δ 7.68-7.70 (1H, m), 7.54-7.61 (2H, m), 7.42-7.48 (1H, m), 4.82 (1H, d, J=12.5 Hz), 4.72 (1H, t, J=3.3 Hz), 4.53 (1H, d, J=12.5 Hz), 3.84-3.92 (1H, m), 3.53-3.60 (1H, m), 1.60-1.95 (6H, m).

후처리

  1. additionwas added
  2. washThe solution was washed with aqueous sodium bicarbonate solution (30 mL) and aqueous sodium chloride solution (30 mL)
  3. dry with materialThe solution was dried over sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-80f0936dc0c4428bb6b8142a668723df
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06933304B2

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