Methyltriphenylphosphonium iodide → HCID 89393436, compound

HRID 572644Notes

Reaction equation

HRID 572644 reaction equation
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Si:22]([O:29][CH2:30][CH2:31][O:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>C1COCC1>[C:25]([Si:22]([CH3:24])([CH3:23])[O:29][CH2:30][CH2:31][O:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=[CH2:2])=[CH:35][CH:34]=1)([CH3:28])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 638159Methyltriphenylphosphonium iodideHCID 579561014-(2-(Tert-butyldimethylsilyloxy)ethoxy)benzaldehyde

Product 1

HCID 89393436HCID 89393436, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold suspension of methyl triphenyl phosphonium iodide (2.88 g, 7.13 mmol) in THF (20 mL) was added KOBt (0.88 g, 7.84 mmol) slowly. The reaction mixture was warmed to RT and stirred for about 1 h. A solution of 4-(2-(tert-butyldimethylsilyloxy)ethoxy)benzaldehyde (1.0 g, 3.56 mmol) in THF (15 mL) was added slowly to the above reaction mixture and stirred for about another 3 h. The reaction was quenched with water and extracted with diethyl ether (3×75 mL). The combined organic extracts were washed with brine (1×75 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue obtained was purified by silica gel chromatography using 10% EtOAc-hexane as the eluent. Relevant fractions containing the target compound were combined and evaporated to dryness under reduced pressure to afford tert-buyldimethyl (2-(4-vinylphenoxy)ethoxy)silane 0.65 g, (65%), 1H NMR (400 MHz, CDCl3): δ 7.350-7.342 (d, J=3.2 Hz, 2H), 6.882-6.875 (d, J=2.8 Hz, 2H), 6.857-6.692 (m, 1H), 5.625-5.581 (d, J=17.6 Hz, 1H), 5.132-5.104 (d, J=11.2 Hz, 1H), 4.052-3.954 (m, 4H), 0.909 (s, 9H), 0.1 (s, 6H), MS m/z: 279.3 (M+H)+.

Workup

  1. additionwas added KOBt (0.88 g, 7.84 mmol) slowly
  2. stirringstirred for about another 3 h
  3. customThe reaction was quenched with water
  4. extractionextracted with diethyl ether (3×75 mL)
  5. washThe combined organic extracts were washed with brine (1×75 mL)
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue obtained
  9. customwas purified by silica gel chromatography
  10. additionRelevant fractions containing the target compound
  11. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7d462a5ab4b8408a9f4bc30146e39c9c
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

Loading…