Triethylamine → Diethyl 4-((methoxycarbonyl)(phenyl)methyl)phenylphosphonate

HRID 1525243Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[CH2:19]([O:21][P:22]([O-:26])[O:23][CH2:24][CH3:25])[CH3:20].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:12][O:11][C:9]([CH:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:5]1[CH:6]=[CH:7][C:2]([P:22](=[O:26])([O:23][CH2:24][CH3:25])[O:21][CH2:19][CH3:20])=[CH:3][CH:4]=1)=[O:10]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of compound Methyl 2-(4-bromophenyl)-2-phenylacetate, 14-d, (1.52 g, 5.0 mmol), diethylphosphite (2.42 g, 17.5 mmol) and triethylamine (3.13 g, 31 mmol) in toluene (20 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dicholoropalladium (100 mg). The mixture was allowed to stir overnight at 110° C. and filtrated. The solution was concentrated to afford the crude product which was purified by column chromatography to give compound 14-e as colorless oil (1.7 g, 94%). 1H NMR (300 MHz, CDCl3) δ1.29-1.35 (m, 6H), 3.73 (s, 3H), 4.10-4.13 (m, 4H), 5.03 (s, 1H), 7.23-7.40 (m, 7H), 7.69-7.77 (m, 2H). LC-MS: (M+H)+ 363.

Workup

filtrationfiltrated
concentrationThe solution was concentrated
customto afford the crude product which
customwas purified by column chromatography

Sources & evidence

ORD record: ord-d5868aed4c4b43c49d66d73b839d5760
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079930B2

Reaction notes

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