3,4-dihydro-2H-pyran → 5-(Oxiran-2-yl)pentan-1-ol

HRID 1263275노트

반응식

HRID 1263275 반응식
Br[CH2:2][CH:3]([OH:10])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].O1C=CCCC1>C(Cl)Cl.CCOCC.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1>[O:10]1[CH2:2][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9]

참가 물질

6

반응물 2

HCID 80803,4-dihydro-2H-pyranHCID 133660747-Bromo-6-hydroxy-1-heptanol

생성물 1

HCID 136166735-(Oxiran-2-yl)pentan-1-ol수율 225.1%

시약·촉매·용매 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)촉매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

A solution of 4 (123 mg, 0.58 mmol) and dihydropyran (0.22 mL, 2.33 mmol) in methylene chloride (2 mL) containing pyridinium tosylate (25 mg, 0.1 mmol) was stirred at room temperature for 20 hours. It was diluted with ether and washed with saturated aqueous sodium chloride. The separated aqueous layer was extracted once with ether and the combined ether layer was dried over magnesium sulfate. The crude product was purified on a silica gel column to give 170 mg of 7-bromo-1,6-bistetrahydropyranyl heptanyl ether (6). PMR (CDCl3): δ4.86-4.48 (m, 2H), 4.00-3.41 (m, 9H), 1.93-1.18 (m, 20H).

후처리

  1. washwashed with saturated aqueous sodium chloride
  2. extractionThe separated aqueous layer was extracted once with ether
  3. dry with materialthe combined ether layer was dried over magnesium sulfate
  4. customThe crude product was purified on a silica gel column

출처 및 근거

ORD 기록
ord-984ddc202ccd44b4a78ec63362fed47d
출처 데이터셋
uspto-grants-1984_06
특허 번호
US04456613

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