2-Bromoethyl methyl ether → HCID 89498326, compound

HRID 1430280Notes

Reaction equation

HRID 1430280 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]1.C([N-]C(C)C)(C)C.[Li+].Br[CH2:22][CH2:23][O:24][CH3:25]>O1CCCC1.CCOCC>[CH3:25][O:24][CH2:23][CH2:22][C:4]1([C:8]([O:10][CH3:11])=[O:9])[CH2:5][CH2:6][CH2:7][C:2]([CH3:12])([CH3:1])[CH2:3]1

Participants

6

Reactant 3

HCID 809722-Bromoethyl methyl etherHCID 2724682Lithium diisopropylamideHCID 6428760HCID 6428760, compound

Product 1

HCID 89498326HCID 89498326, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of EXAMPLE 146B (0.60 g) in tetrahydrofuran (5 mL) was added to lithium diisopropylamide (2.0 M, 2.10 mL) at −78° C. After stirring for 30 minutes, 1-bromo-2-methoxyethane (0.64 g) was added and the reaction mixture was allowed to warm to room temperature. The reaction mixture was diluted with ether (75 mL), washed with water (50 mL) and brine (50 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with 1-20% ethyl acetate in hexanes provided the title compound.

Workup

  1. washwashed with water (50 mL) and brine (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washSilica gel chromatography eluting with 1-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d83142c469b844c39a94a8711064b26e
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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