2,2-Bis(diphenylphosphinomethyl)-3-cyclopenta-dienyl-1-propanol → 3-Cyclopentadienyl-2-(5-dibenzophospholylmethyl)-2-(diphenylphosphinomethyl)-1-propanol

HRID 1276822Notes

Reaction equation

HRID 1276822 reaction equation
[C:1]1([P:7]([CH2:14][C:15]([CH2:24][P:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH2:18][C:19]2[CH2:23][CH:22]=[CH:21][CH:20]=2)[CH2:16][OH:17])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(CC2(CP(C3C=CC=CC=3)C3C=CC=CC=3)COC2)C=CC=C1.[Li]CCCC.[C-]1C2C3C=CC=CC=3PC=2C=CC=1.[Li+]>>[CH:19]1([CH2:18][C:15]([CH2:14][P:7]2[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:6]3[CH:5]=[CH:4][CH:3]=[CH:2][C:1]2=3)([CH2:24][P:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:16][OH:17])[CH:23]=[CH:22][CH:21]=[CH:20]1

Participants

5

Reactant 4

HCID 153975922,2-Bis(diphenylphosphinomethyl)-3-cyclopenta-dienyl-1-propanolHCID 129671872HCID 129671872, compoundHCID 1317222463-(Cyclopentadienylmethyl)-3-(diphenylphosphino-methyl)oxetaneHCID 178418339Butyllithium

Product 1

HCID 1317222453-Cyclopentadienyl-2-(5-dibenzophospholylmethyl)-2-(diphenylphosphinomethyl)-1-propanol

Procedure

The preparation was carried out using a method similar to that for 3a. 1.6 g (4.8 mmol) of 2a were deprotonated with 2 ml (4.8 mmol) of n-BuLi solution and reacted with 1.2 equivalents of lithium dibenzophospholide solution to give the crude product 3c. The colorless oil which remained was dissolved in methylene chloride and absorbed on kieselguhr. This was followed by flash chromatography on silica gel (23*4 cm; eluant: PE/diethyl ether in a ratio of 8.5:1.5, RF =0.27). This gave 1.36 g (55%) of 3c in the form of a colorless, viscous oil.

Sources & evidence

ORD record
ord-1a9f7612964a4811966d897ce5ec5c59
Source dataset
uspto-grants-2000_12
Patent number
US06166234

Reaction notes

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