Bis(dichloromethyl) ether → HCID 57424221, compound

HRID 1869874Notes

Reaction equation

HRID 1869874 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([CH3:17])([CH3:16])[CH2:10][C:9]2([CH3:19])[CH3:18])=[O:5])[CH3:2].Cl[CH:21]([O:23]C(Cl)Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([CH:21]=[O:23])[CH:15]=1)[O:12][C:11]([CH3:17])([CH3:16])[CH2:10][C:9]2([CH3:18])[CH3:19])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 558102Bis(dichloromethyl) etherHCID 12136999HCID 12136999, compound2×

Product 1

HCID 57424221HCID 57424221, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred, cooled (ice bath) solution of 2,2,4,4-tetramethyl-chroman-6-carboxylic acid ethyl ester (Intermediate 36, 0.5 g, 1.92 mmol) in anhydrous dichloromethane (10 mL) was treated with titanium tetrachloride (0.4 mL, 3.26 mmol) followed by ∀,∀-dichloromethyl ether (0.17 mL, 1.92 mmol). The reaction was allowed to warm to ambient temperature over 2 days, quenched cautiously with ice and water and extracted with dichloromethane. The organic extract was washed with water and brine, dried over sodium sulfate, filtered and evaporated in vacuo to a residue that was subjected to flash column chromatography to afford the title compound (0.11 g, 20%).

Workup

  1. customquenched cautiously with ice and water
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to a residue that

Sources & evidence

ORD record
ord-74b1fc9fde2346ebb520d3e0ceb10c30
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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