Triphenylphosphine → (1,4-Dioxa-spiro[4.5]dec-8-ylmethyl)triphenylphosphoniumiodide

HRID 221223Notes

Reaction equation

HRID 221223 reaction equation
[I:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]1.[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C>[I-:1].[O:10]1[C:6]2([CH2:11][CH2:12][CH:3]([CH2:2][P+:19]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:4][CH2:5]2)[O:7][CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 219590588-(Iodomethyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 86646422(1,4-Dioxa-spiro[4.5]dec-8-ylmethyl)triphenylphosphoniumiodide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.54 g of 8-iodomethyl-1,4-dioxa-spiro[4.5]decane and 5.15 g of triphenylphosphine are dissolved in 32 ml of acetonitrile and heated at the boil under reflux for 12 hours. The mixture is stirred at room temperature for two days and then concentrated under reduced pressure to a volume of about 15 ml, and 30 ml of diethyl ether are added. With vigorous stirring in an ice-bath, a precipitate begins to form. The precipitate is filtered off with suction and dried under reduced pressure. This gives 3.86 g of (1,4-dioxa-spiro[4.5]dec-8-ylmethyl)triphenylphosphoniumiodide.

Workup

  1. temperatureheated at the boil
  2. temperatureunder reflux for 12 hours
  3. concentrationconcentrated under reduced pressure to a volume of about 15 ml, and 30 ml of diethyl ether
  4. additionare added
  5. stirringWith vigorous stirring in an ice-bath
  6. customto form
  7. filtrationThe precipitate is filtered off with suction
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-ead9dce635544d3099587d9a8a1441e6
Source dataset
uspto-grants-2012_06
Patent number
US08207146B2

Reaction notes

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