Triethyl phosphite → HCID 59526931, compound

HRID 384438Notes

Reaction equation

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

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 108278984-(Benzyloxy)-2-(chloromethyl)-3-methylquinoline

Product 1

HCID 59526931HCID 59526931, compoundYield 83.5%

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-(benzyloxy)-2-(chloromethyl)-3-methylquinoline (1.00 g) and triethyl phosphite (3.84 g) was stirred at 150° C. for 6 hours. The reaction mixture was allowed to cool to room temperature, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=98/2) to obtain diethyl {[4-(benzyloxy)-3-methylquinolin-2-yl]methyl}phosphonate (1.12 g).

Workup

temperatureto cool to room temperature
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=98/2)

Sources & evidence

ORD record: ord-dc64679c71294217b503346ffa11e02e
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367702B2

Reaction notes

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