Triphenylphosphine → HCID 11135065, compound

HRID 1929328Notes

Reaction equation

[Br:1][CH2:2][CH2:3][CH2:4][O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[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>C1C=CC=CC=1>[Br-:1].[Si:6]([O:5][CH2:4][CH2:3][CH2:2][P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 1-bromo-3-[(tert-butyldimethylsilyl)oxy]propane (2.18 g, 8.56 mmol) in anhydrous benzene (1.6 mL) was added triphenylphosphine (2.64 g, 10.2 mmol) under argon with stirring. The mixture was heated at 85° C. for 18 hours and cooled to room temperature. The liquid was decanted and the solid residue was grounded with spatula, filtered, and washed several times with ether. Colorless crystals of phosphonium salt B (3.7 g) were purified by silica column chromatography. Pure salt B (3.04 g, 69%) was eluted with chloroform/methanol (96:4). B: 1H NMR (500 MHz, CDCl3) δ0.039 (6H, s, 2×SiCH3), 0.857 (9H, s, Si-t-Bu), 1.93 (2H, m, CH2—CH2—CH2), 3.86-3.94 (4H, br m, CH2—CH2—O and P—CH2), 7.70, 7.79 and 7.85 (6H, 3H and 6H, each m, Ar—H).

Workup

temperaturecooled to room temperature
customThe liquid was decanted
filtrationfiltered
washwashed several times with ether
customColorless crystals of phosphonium salt B (3.7 g) were purified by silica column chromatography
washPure salt B (3.04 g, 69%) was eluted with chloroform/methanol (96:4)

Sources & evidence

ORD record: ord-33e3b764727443eca5e2cd25d35989e6
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188064B2

Reaction notes

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