4-Methylmorpholine → HCID 86637897, compound

HRID 2389322Notes

Reaction equation

HRID 2389322 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:19]([O:23][CH3:24])(=[O:22])[C:20]#[CH:21].CN1CCOCC1>CC#N>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[O:18]/[CH:21]=[CH:20]/[C:19]([O:23][CH3:24])=[O:22])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 13536Methyl propiolateHCID 68536344HCID 68536344, compound

Product 1

HCID 86637897HCID 86637897, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)phenol (1.78 g) in MeCN (10 mL) were added methyl propiolate (0.667 mL) and NMM (0.0441 mL) at ambient temperature and the mixture was stirred at the same temperature for 3 hours. The solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=97:3) to afford methyl (2E)-3-[3-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)phenoxy]-acrylate (1.80 g) as a colorless oil.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=97:3)

Sources & evidence

ORD record
ord-a2a72c42198f466bbb00d2338d142eb2
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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