HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

(2'-Methoxyethoxymethoxy-[1,1';3'1'']terphenyl-5'-yloxy)butane → 5'-Butoxy-[1,1';3',1'']terphenyl-2'-ol

HRID 1884692
Notes
Print preview

Reaction equation

HRID 1884692 reaction equation
COCCOC[O:7][C:8]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][C:11]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:10][C:9]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl.CCOC(C)=O.[Zn+2].[Br-].[Br-]>[CH2:21]([O:20][C:11]1[CH:12]=[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]([OH:7])=[C:9]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:10]=1)[CH2:22][CH2:23][CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 131722493(2'-Methoxyethoxymethoxy-[1,1';3'1'']terphenyl-5'-yloxy)butane

Product 1

HCID 222376275'-Butoxy-[1,1';3',1'']terphenyl-2'-olYield 92.7%

Reagents, catalysts & solvents 3

HCID 10421208Zinc bromideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (2′-methoxyethoxymethoxy-[1,1′;3′,1″]terphenyl-5′-yloxy)butane (0.237 g, 0.583 mmol) in CH2Cl2 (6 mL) at room temperature was added anhydrous ZnBr2 (0.656 g, 2.92 mmol). After 18 h at this temperature, the resulting mixture was diluted with EtOAc (100 mL). The organic layer was washed with sat. aq. NaHCO3 (10 mL) and brine (10 mL) and then dried (MgSO4). After concentration, the residue was purified by preparatory plate chromatography (10% EtOAc/petroleum ether) to afford the product (0.172 g, 92%) as a solid; 1H NMR (CDCl3) δ 0.97 (t, J=10.9 Hz, 3H), 1.39-1.60 (m, 2H), 1.68-1.87 (m, 2H), 3.97 (t, J=9.5 Hz, 2H), 5.05 (s, 1H), 6.87 (s, 2H), 7.32-7.62 (m, 10H); mass spectrum [(+) ESI], m/z 319 (M+H)+, 341 (M+Na)+.

Workup

  1. washThe organic layer was washed with sat. aq. NaHCO3 (10 mL) and brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationAfter concentration
  4. customthe residue was purified by preparatory plate chromatography (10% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-fb2749b1eeb24a069bed83f32696c2bc
Source dataset
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06765021B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes