Methane, dichloromethoxy- → 6-fluorochroman-8-carbaldehyde

HRID 1738891Notes

Reaction equation

HRID 1738891 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][CH2:5]2.[CH3:12][O:13]C(Cl)Cl>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH:12]=[O:13])[CH:11]=1)[O:8][CH2:7][CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 114691696-fluorochroman

Product 1

HCID 112291326-fluorochroman-8-carbaldehydeYield 108.8%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

13.74 g (90.28 mmol) of 6-fluorochroman are dissolved in 250 ml of methylene chloride. The whole is cooled to 0° C. and 20.15 ml (0.18 mol) of TiCl4 are added dropwise. The solution becomes brown and is stirred for 10 minutes at room temperature. 8.78 ml (99.3 mmol) of α,α-dichloromethyl ether are then introduced. The whole is stirred overnight at room temperature, poured into ice-cold water and decanted. The organic phase is dried and evaporated to yield 17.7 g of a residue which is purified by chromatography on silica (eluant CH2Cl2 /cyclohexane: 50/50). 6.3 g of the expected product are obtained. Yield: 38.7%.

Workup

  1. stirringThe whole is stirred overnight at room temperature
  2. additionpoured into ice-cold water
  3. customdecanted
  4. customThe organic phase is dried
  5. customevaporated

Sources & evidence

ORD record
ord-186ac148afc24b12a2644dc07ed361cf
Source dataset
uspto-grants-1999_10
Patent number
US05965575

Reaction notes

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