3,4-dihydro-2H-pyran → 2-(4-Bromobutoxy)tetrahydro-2H-pyran

HRID 39246

반응식

HRID 39246 반응식
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.ClCCl>[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1

참가 물질

5

반응물 2

HCID 80803,4-dihydro-2H-pyranHCID 1183884-Bromobutanol

생성물 1

HCID 5590192-(4-Bromobutoxy)tetrahydro-2H-pyran수율 92.3%

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 6344Dichloromethane용매

실험 절차

3,4-Dihydro-2H-pyran (8.5 mL, 90.96 mmol) was added dropwise to the dichloromethane (20 mL) solution of 1 (10.7 g, 69.93 mmol) and p-toluenesulfonic acid monohydrate (26.5 mg, 0.1372 mmol). The mixture was stirred at room temperature over night. After removing the solvent, the residue was purified by flash chromatography on silica gel with 5:1 hexanes/ethyl acetate as the eluent to yield product 2 as a colorless oil (15.3 g, 92%). 1H NMR (400 MHz, CDCl3): δ 1.48-1.62 (m, 4H), 1.68-1.85 (m, 4H), 1.94-2.02 (m, 2H), 3.40-3.53 (m, 4H), 3.74-3.88 (m, 2H), 4.57-4.59 (m, 1H).

후처리

  1. customAfter removing the solvent
  2. customthe residue was purified by flash chromatography on silica gel with 5:1 hexanes/ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-4df15ee16ba343d6858c801aa90a4577
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524691B2

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