Sodium Chloride → methyl N-[2-chloro-5-(3-hydroxy-3-methyl-1-butynyl)benzyl]carbamate

HRID 427247Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:14])=[C:6]([CH:13]=1)[CH2:7][NH:8][C:9](=[O:12])[O:10][CH3:11].[CH3:15][C:16]([OH:20])([C:18]#[CH:19])[CH3:17].[Cl-].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C(N(CC)CC)C>[Cl:14][C:5]1[CH:4]=[CH:3][C:2]([C:19]#[C:18][C:16]([OH:20])([CH3:17])[CH3:15])=[CH:13][C:6]=1[CH2:7][NH:8][C:9](=[O:12])[O:10][CH3:11]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture comprising 3.50 g of methyl N-(5-bromo-2-chlorobenzyl)carbamate, 2.11 g of 2-methyl-3-butyn-2-ol, 0.79 g of dichlorobis(triphenylphosphine)palladium, 0.38 g of copper(I) iodide and 40 ml of triethylamine, was stirred at 90° C. for 30 hours in an autoclave. This reaction solution was poured into a saturated sodium chloride aqueous solution and extracted with ethyl acetate, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 3.03 g of methyl N-[2-chloro-5-(3-hydroxy-3-methyl-1-butynyl)benzyl]carbamate as a brown viscous liquid.

Workup

extractionextracted with ethyl acetate
dry with materialby drying over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-b5930c8359604aff81ded6cf72569441
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313071B1

Reaction notes

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