3,4-dihydro-2H-pyran → 3-Chloro-2-tetrahydropyranyloxy-1-propyl acetate

HRID 1075309

반응식

HRID 1075309 반응식
[C:1]([O:4][CH2:5][CH:6]([OH:9])[CH2:7][Cl:8])(=[O:3])[CH3:2].[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[C:1]([O:4][CH2:5][CH:6]([O:9][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][O:10]1)[CH2:7][Cl:8])(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 80803,4-dihydro-2H-pyranHCID 980693-Chloro-2-hydroxypropyl acetateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

생성물 1

HCID 190484163-Chloro-2-tetrahydropyranyloxy-1-propyl acetate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 271.9 g (1.78 moles) of 3-chloro-2-hydroxy-1-propyl acetate, 244 ml (2.67 moles) of freshly distilled dihydropyran, and 44.7 g (0.178 moles) of pyridinium p-toluenesulfonate in 1800 mL of methylene chloride was stirred at room temperature with cooling to control the reaction exotherm. After 22 hours the reaction mixture was washed with 500 mL of water and 250 mL of sodium chloride solution, and was dried over sodium sulfate. Solvent was removed and the residue was dried at 0.03 mm for 1.5 hours to give 473.3 g of crude 3-chloro-2-tetrahydropyranyloxy-1-propyl acetate: 1H NMR (CDCl3) δ1.63 (br. s, 6 H, (CH2)3); 2.08 (s, 3H, CH3CO); 3.5-4.3 (7H, CH2CHCH2); 4.73 (br. s, 1H, --O--CH); IR (neat, NaCl) 3000, 2910 (C--H); 1740 cm- 1 (--O--CO--CH3).

후처리

  1. temperaturewith cooling
  2. customthe reaction exotherm
  3. washAfter 22 hours the reaction mixture was washed with 500 mL of water and 250 mL of sodium chloride solution
  4. dry with materialwas dried over sodium sulfate
  5. customSolvent was removed
  6. customthe residue was dried at 0.03 mm for 1.5 hours

출처 및 근거

ORD 기록
ord-6da761fed5ce46139d12240f4f8561a4
출처 데이터셋
uspto-grants-1983_07
특허 번호
US04395561

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