Hydrochloric Acid → HCID 58071511, compound

HRID 1256026Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([P:12]2(=[O:28])[CH2:17][CH2:16][C:15](C(OCC)=O)([C:18]([O:20]CC)=[O:19])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[OH-].[Li+].O.Cl>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([P:12]2(=[O:28])[CH2:13][CH2:14][CH:15]([C:18]([OH:20])=[O:19])[CH2:16][CH2:17]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

Conditions

Temperature: 75 °C

Procedure

Diethyl 1-(3-methoxy-4-nitrophenyl)phosphinane-4,4-dicarboxylate 1-oxide (INTERMEDIATE 59) (4.5 g, 10.89 mmol) and lithium hydroxide (1.043 g, 43.55 mmol) were added to a 200-mL round bottomed flask. Water (30 mL) and THF (30 mL) were added to give a brown suspension. The mixture was heated to 75° C. and stirred at that temperature for 4 h. The reaction mixture was concentrated to give a solid residue. To the mixture was added HCl (aq., 4 N, 60 mL) to give a suspension and further diluted with THF (30.0 mL). The mixture was microwaved at 110° C. for 2 h. After cooling to RT, water (60 mL) was added to the reaction solution. The solution was extracted with 30% iPrOH in chloroform (5×40 mL), and the combined organic layers were concentrated to give the title compound (0.4 g, 12% yield). m/z 314.

Workup

customto give a brown suspension
concentrationThe reaction mixture was concentrated
customto give a solid residue
customto give a suspension
customThe mixture was microwaved at 110° C. for 2 h
temperatureAfter cooling to RT
extractionThe solution was extracted with 30% iPrOH in chloroform (5×40 mL)
concentrationthe combined organic layers were concentrated

Sources & evidence

ORD record: ord-2a220e97c29c4ebebb8436431acc7108
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461170B2

Reaction notes

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