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

HRID 1263275Notes

Reaction equation

HRID 1263275 reaction equation
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]

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-984ddc202ccd44b4a78ec63362fed47d
Source dataset
uspto-grants-1984_06
Patent number
US04456613

Reaction notes

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