Triethyl phosphite → HCID 86629706, compound

HRID 384594Notes

Reaction equation

Br[CH2:2][CH2:3][CH:4]([C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:28])[C:24]([OH:27])([CH3:26])[CH3:25])=[CH:19][CH:18]=1)[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:16])[C:12]([OH:15])([CH3:14])[CH3:13])=[CH:7][CH:6]=1.[P:29]([O:36]CC)([O:33][CH2:34]C)[O:30][CH2:31]C>>[CH3:31][O:30][P:29]([CH2:2][CH2:3][CH:4]([C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:28])[C:24]([OH:27])([CH3:26])[CH3:25])=[CH:19][CH:18]=1)[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:16])[C:12]([CH3:14])([OH:15])[CH3:13])=[CH:7][CH:6]=1)(=[O:36])[O:33][CH3:34]

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 68861820HCID 68861820, compound

Product 1

HCID 86629706HCID 86629706, compoundYield 106.8%

Procedure

1-(4-{3-Bromo-1-[4-(2-hydroxy-2-methylpropionyl)phenyl]propyl}phenyl)-2-hydroxy-2-methylpropan-1-one (5.0 g, 0.0112 moles) is reacted with 4.6 grams of triethyl phosphite following the procedure of Example 23 to give 5.7 g (98% yield) of {3,3-bis-[4-(2-hydroxy-2-methylpropionyl)phenyl]propyl}phosphonic acid dimethyl ester, a yellow oil. The ester is reacted with trimethylsilyl bromide in chloroform and methanol, following the procedure of Example 22, to give 5.0 g of the title compound, an amorphous solid.

Sources & evidence

ORD record: ord-3c35e26021634d10b1486c0001e96c26
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367743B2

Reaction notes

Loading…