Acetyl chloride → HCID 101043386, compound

HRID 2390280Notes

Reaction equation

[C:1]([O:5][C:6](=[O:25])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[C:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1)([CH3:4])([CH3:3])[CH3:2].[C:26](Cl)(=[O:28])[CH3:27]>>[C:1]([O:5][C:6](=[O:25])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[C:17][C:18]1[CH:19]=[CH:20][C:21]([NH:24][C:26](=[O:28])[CH3:27])=[CH:22][CH:23]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 58522032HCID 58522032, compound2×

Product 1

HCID 101043386HCID 101043386, compoundYield 91%

Procedure

Following the general method as outlined in Intermediate 223, starting from tert-butyl{2-[(4-aminophenyl)ethynyl]-4-chlorophenoxy}acetate (Intermediate 222) and acetyl chloride, the title compound was obtained in 91% yield after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record: ord-7807966062004000962325204681fc87
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273769B2

Reaction notes

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