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

HRID 1263275ノート

反応式

HRID 1263275 の反応式
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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)触媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-984ddc202ccd44b4a78ec63362fed47d
出典データセット
uspto-grants-1984_06
特許番号
US04456613

反応ノート

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