Diethyl Ether → Triphenyl[(tetrahydro-2H-pyran-4-yl)methyl]phosphonium iodide

HRID 729696Notes

Reaction equation

HRID 729696 reaction equation
[I:1][CH2:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[CH:9]1[CH:14]=[CH:13][C:12]([P:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][CH:10]=1.CCOCC>CC#N>[I-:1].[C:22]1([P+:15]([C:12]2[CH:11]=[CH:10][CH:9]=[CH:14][CH:13]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:2][CH:3]2[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 27955074-(Iodomethyl)oxane

Product 1

HCID 21094223Triphenyl[(tetrahydro-2H-pyran-4-yl)methyl]phosphonium iodide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

A stirred solution of 4-iodomethyltetrahydropyran (3.43 g, 15.2 mmol) and PPh3 (3.98 g, 15.2 mmol) in anhydrous MeCN (10 mL) was heated under reflux for 19 h. On cooling to 20° C., Et2O (50 mL) was added. The precipitate formed was collected, washed with Et2O (150 mL), and recrystallised (MeCN) to give the title compound: m/z (ES+)=361.2 [M]+.

Workup

  1. temperatureunder reflux for 19 h
  2. customThe precipitate formed
  3. customwas collected
  4. washwashed with Et2O (150 mL)
  5. customrecrystallised (MeCN)

Sources & evidence

ORD record
ord-aae6637dee5a436f8f1ab5a429671fa3
Source dataset
uspto-grants-2009_09
Patent number
US07582632B2

Reaction notes

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