Sodium Iodide → HCID 86608406, compound

HRID 1363989Notes

Reaction equation

HRID 1363989 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C:9]1[C:14]([O:15][CH3:16])=[C:13]([O:17][CH3:18])[C:12]([O:19][CH3:20])=[C:11]([O:21][CH3:22])[C:10]=1[CH3:23])(=O)=O.[C:24]1([P:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Na+].[I-:44]>C(Cl)Cl>[I-:44].[CH3:16][O:15][C:14]1[C:13]([O:17][CH3:18])=[C:12]([O:19][CH3:20])[C:11]([O:21][CH3:22])=[C:10]([CH3:23])[C:9]=1[CH2:8][CH2:7][CH2:6][P+:30]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 11776TriphenylphosphineHCID 58987887HCID 58987887, compound

Product 1

HCID 86608406HCID 86608406, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude methanesulfonate 4 (3.30 g, 9.8 mmol) was used directly in the following reaction by mixing with a freshly ground mixture of triphenylphosphine (4.08 g, 15.6 mmol) and NaI (7.78 g, 51.9 mmol) in a Kimax tube and sealed under argon. The mixture was then held at 70-74° C. with magnetic stirring for 3 hrs during which time the mixture changed from a molten thick liquid into a glassy solid. The tube was cooled to room temperature and the residue stirred with CH2Cl2 (30 mL). The suspension was then filtered and the filtrate evaporated in vacuo. The residue was dissolved in a minimum amount of CH2Cl2 and triturated with excess ether (250 mL) to precipitate the white solid. The solid was filtered and washed with ether, dried in vacuo to give pure [3-(2,3,4,5-tetramethoxy-6-methyl-phenyl)-propyl]triphenylphosphonium iodide (5) (5.69 g, 90%). 1H NMR δ 7.82-7.65 (15H, m, Ar—H), 3.88, 3.86, 3.74, 3.73 (12H, s, OMe), 3.76-3.88 (2H, m, CH2—P+), 2.98 (2H, t, J=7.0 Hz, CH2—Ar), 2.13 (3H, s, Ar-Me), 1.92-1.78 (2H, m, —CH2—) ppm. 31P NMR (121.4 MHz) δ 25.32 ppm. Anal. calcd. for C32H36IO5P: C, 59.8; H, 5.7; P, 4.8. Found: C, 59.8; H, 5.8; P, 4.5%.

Workup

  1. customsealed under argon
  2. customwas then held at 70-74° C.
  3. filtrationThe suspension was then filtered
  4. customthe filtrate evaporated in vacuo
  5. dissolutionThe residue was dissolved in a minimum amount of CH2Cl2
  6. customtriturated with excess ether (250 mL)
  7. customto precipitate the white solid
  8. filtrationThe solid was filtered
  9. washwashed with ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-3b3ff3668b2042aeac5ed166622a685a
Source dataset
uspto-grants-2011_02
Patent number
US07888335B2

Reaction notes

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