Diethyl Ether → HCID 13436793, compound

HRID 638409Notes

Reaction equation

HRID 638409 reaction equation
COCC=C[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH3:13][C:14]([O:17]O)(C)[CH3:15].CC[O:21][CH2:22]C.[O-]S([O-])(=O)=O.[Na+].[Na+].C(Cl)[Cl:32]>Cl[Ti](Cl)(Cl)Cl>[CH3:22][O:21][CH2:13][CH:14]([OH:17])[CH:15]([Cl:32])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH3:6]

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 6410tert-Butyl hydroperoxideHCID 24436Sodium SulfateHCID 53651719HCID 53651719, compound

Product 1

HCID 13436793HCID 13436793, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

Optimization of reaction conditions resulted in the following recommended procedure, illustrated for 1-methoxydec-2-ene as substrate. To a -78° solution of the substrate (0.1654 g, 0.92 mmole) in 20 ml CH2Cl2, under N2, was added TBHP (1.2 eq.), followed by TiCl4 (1.2 eq.). The reaction was worked up after 5 hr by pouring the cooled solution into Et2O/sat. Na2SO4 and allowing to stir for 1 hr. Separation of layers and purification of the crude product by chromatography resulted in a 92% yield of 1-methoxy-2-hydroxy-3-chlorodecane, with the chlorohydrin in the threo configuration.

Workup

  1. customOptimization of reaction conditions
  2. customresulted in the
  3. customSeparation of layers and purification of the crude product by chromatography

Sources & evidence

ORD record
ord-2631472e16e048bc9f2a952ad624cc56
Source dataset
uspto-grants-1985_12
Patent number
US04560811

Reaction notes

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