4-Chlorobenzaldehyde → HCID 86703245, compound

HRID 2204424Notes

Reaction equation

[Li+].CC([N-]C(C)C)C.[CH:9]1([N:12]2[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:20])=[O:18])=[CH:13]2)[CH2:11][CH2:10]1.[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=1>C1COCC1>[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]([OH:27])[C:13]2[N:12]([CH:9]3[CH2:10][CH2:11]3)[CH:16]=[CH:15][C:14]=2[C:17]([O:19][CH3:20])=[O:18])=[CH:24][CH:23]=1

Participants

Conditions

Temperature: -50 °C

Procedure

LDA (1.8M, 18.97 mL, 34.2 mmol) was added dropwise to a solution of methyl 1-cyclopropyl-1H-pyrrole-3-carboxylate (Step 240.6) (4.03 g, 24.40 mmol) in THF (80 mL) at −78° C. and the mixture was stirred for 30 min. A solution of 4-chlorobenzaldehyde (3.77 g, 26.8 mmol) in THF (20 mL) was added at −78° C. The mixture was allowed to warm to −50° C. over 2 hrs, quenched with a saturated aqueous solution of ammonium chloride, and taken up in EtOAc/saturated ammonium chloride solution. The aqueous layer was separated and extracted twice with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), and concentrated. The crude material was purified by silica gel column chromatography (hexane/EtOAc 4:1) to afford the title compound (6.1 g, 79% yield) as a yellow solid. TLC (hexane/EtOAc 4:1): Rf=0.21.

Workup

customquenched with a saturated aqueous solution of ammonium chloride
customThe aqueous layer was separated
extractionextracted twice with EtOAc
washThe combined organic extracts were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe crude material was purified by silica gel column chromatography (hexane/EtOAc 4:1)

Sources & evidence

ORD record: ord-c0777c08c295425989dc9acde0889264
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365576B2

Reaction notes

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