Tetrabutylammonium Fluoride → 2-(4-Chlorophenyl)-N-(4'-hydroxy-3'-methoxy-biphenyl-2-yl)-2-prop-2-ynyloxy-acetamide

HRID 1375223

Reaction equation

HRID 1375223 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:19][C:20](=[O:33])[CH:21]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[O:22][CH2:23][C:24]#[CH:25])=[CH:9][C:8]=1[O:34][CH3:35])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([CH:21]([O:22][CH2:23][C:24]#[CH:25])[C:20]([NH:19][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:10]2[CH:11]=[CH:12][C:7]([OH:6])=[C:8]([O:34][CH3:35])[CH:9]=2)=[O:33])=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 21079853N-[4'-(tert-butyl-diphenyl-silanyloxy)-3'-methoxy-biphenyl-2-yl]-2-(4-chlorophenyl)-2-prop-2-ynyloxy-acetamide

Product 1

HCID 210798502-(4-Chlorophenyl)-N-(4'-hydroxy-3'-methoxy-biphenyl-2-yl)-2-prop-2-ynyloxy-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 10.2 g (15.5 mmol) N-[4′-(tert-butyl-diphenyl-silanyloxy)-3′-methoxy-biphenyl-2-yl]-2-(4-chlorophenyl)-2-prop-2-ynyloxy-acetamide and 24.5 g (77.5 mmol) tetrabutylammonium fluoride in 200 ml of dichloromethane is stirred for 4 hours at room temperature. After extracting with water/ethyl acetate and evaporation of the organic phase, the residue is subjected to flash-chromatography (ethyl acetate/hexane 4:6). Yield: 2-(4-chlorophenyl)-N-(4′-hydroxy-3′-methoxy-biphenyl-2-yl)-2-prop-2-ynyloxy-acetamide, m.p. 140–142° C.

Workup

  1. extractionAfter extracting with water/ethyl acetate and evaporation of the organic phase

Sources & evidence

ORD record
ord-2d23ba3080534274a942c4ce53d85812
Source dataset
uspto-grants-2007_01
Patent number
US07166746B2

Linked notes

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