Tetrahydrofuran → Methanone, (2-nitrophenyl)phenyl-

HRID 965271Notes

Reaction equation

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

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 118752-Nitrobenzoyl chloride

HCID 178418339Butyllithium

Product 1

HCID 137514Methanone, (2-nitrophenyl)phenyl-

Conditions

Temperature: -78 °C

Procedure

1-Scheme 1 (1.0 g, 1.0 mmol) was suspended in THF (10 mL) and cooled to -78° C. Added n-BuLi (1.6M in Hexanes, 1.6 mmol) and allowed to react for 2 h. The mixture was warmed to -65° C.; 2-nitrobenzoyl chloride (1 mL, 7 mmol) was added, and the mixture was allowed to warm to room temperature overnight. Filtration followed by washing with methanol (3×25 mL), water (2×25 mL, methylene chloride (2×25 mL and finally with methanol (50 mL) gave the resin which was dried at 60° C. in vacuo. Recovered (1.0 g). IR 1740, 1520 cm-1.

Workup

customto react for 2 h
temperatureThe mixture was warmed to -65° C.
temperatureto warm to room temperature overnight
filtrationFiltration
washby washing with methanol (3×25 mL), water (2×25 mL, methylene chloride (2×25 mL
customfinally with methanol (50 mL) gave the resin which
customwas dried at 60° C. in vacuo
customRecovered (1.0 g)

Sources & evidence

ORD record: ord-fa9a1c86c13640e3b1deabbfff0a37e3
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05773512

Reaction notes

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