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

HRID 1075309ノート

反応式

HRID 1075309 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6da761fed5ce46139d12240f4f8561a4
出典データセット
uspto-grants-1983_07
特許番号
US04395561

反応ノート

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