2-Chloromethyl 2-(trimethylsilyl)ethyl ether → HCID 67301822, compound

HRID 643629Notes

Reaction equation

HRID 643629 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C@@H:11]([OH:16])[C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([Br:9])[C:7]=1[OH:8].Cl[CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C@@H:11]([OH:16])[C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([Br:9])[C:7]=1[O:8][CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 67301241HCID 67301241, compound

Product 1

HCID 67301822HCID 67301822, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Under a nitrogen atmosphere 11.1 g (76.6 mmol) 40% KF/Al2O3 were added to a solution of 6.78 g (19.2 mmol) methyl(R)-3-(3,5-dibromo-4-hydroxy-phenyl)-2-hydroxy-propionate in 100 mL acetonitrile and the resulting suspension was stirred for a few minutes at RT. Subsequently a solution of 4.07 mL (23.0 mmol) (2-chloromethoxy-ethyl)-trimethyl-silane in 20 mL acetonitrile was added and the reaction mixture was stirred for 20 h at RT. The mixture was filtered through Celite, the solvent was evaporated down i.vac. and the residue was purified by chromatography (silica gel, n-hexane/EtOAc 7:3).

Workup

  1. stirringthe reaction mixture was stirred for 20 h at RT
  2. filtrationThe mixture was filtered through Celite
  3. customthe solvent was evaporated down i.vac
  4. customand the residue was purified by chromatography (silica gel, n-hexane/EtOAc 7:3)

Sources & evidence

ORD record
ord-83d169a95a1e4bf4a80440df9c0eaff1
Source dataset
uspto-grants-2010_04
Patent number
US07700598B2

Reaction notes

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