4-Nitrobenzaldehyde → HCID 86587324, compound

HRID 723581Notes

Reaction equation

[Cl:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[O:7][CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.C([Li])CCC.[N+:18]([C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1)([O-:20])=[O:19].[Cl-].[NH4+]>CCOCC.O1CCCC1>[Cl:1][C:2]1[S:3][C:4]([C:21]2([N+:18]([O-:20])=[O:19])[CH:22]=[CH:23][C:24]([CH2:25][OH:26])=[CH:27][CH2:28]2)=[CH:5][C:6]=1[O:7][CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-chloro-3-cyclopentyloxythiophene (2.15 g, 10.6 mmol) in ether (27 mL) was added n-butyllithium (2.5 N in hexanes, 4.4 mL, 11 mmol) dropwise at −78° C. under argon. The mixture was allowed to reach 20–25° C. and stirred for 4 hours. After cooling back to −78° C., a solution of p-nitrobenzaldehyde (1.56 g, 10.3 mmol) in tetrahydrofuran (27 mL) was added dropwise. The mixture was stirred at −78° C. for 1 hour. Saturated ammonium chloride was added at −78° C. and the mixture was allowed to reach about 10° C. The crude product was extracted with ethyl acetate, washed with water, brine, dried (Na2SO4), and concentrated to dryness to give 4-(5-chloro-4-cyclopentyloxythien-2-yl)-(4-nitrophenyl)methanol (3.6 g), and was directly used in the next step.

Workup

customto reach 20–25° C.
stirringThe mixture was stirred at −78° C. for 1 hour
customto reach about 10° C
extractionThe crude product was extracted with ethyl acetate
washwashed with water, brine
dry with materialdried (Na2SO4)
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-94ab4f71ba9a4e6cbabd92ae2ba1f6d4
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141584B2

Reaction notes

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