Tin tetrachloride → 6-Methoxy-7-fluoro-2,2-dimethyl-thiochroman-4-one

HRID 619610Notes

Reaction equation

HRID 619610 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:10][C:11]([CH3:17])([CH3:16])[CH2:12][C:13](Cl)=[O:14])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl[Sn](Cl)(Cl)Cl>C(Cl)Cl>[CH3:9][O:8][C:7]1[CH:6]=[C:5]2[C:4](=[CH:3][C:2]=1[F:1])[S:10][C:11]([CH3:17])([CH3:16])[CH2:12][C:13]2=[O:14]

Participants

4

Reactant 2

HCID 24287Tin tetrachlorideHCID 179218173-(3-Fluoro-4-methoxy-phenysulfanyl)-3-methyl-butyroyl chloride

Product 1

HCID 218466566-Methoxy-7-fluoro-2,2-dimethyl-thiochroman-4-oneYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the acyl chloride (Compound 202, 2.80 g, 10.1 mmol) in 35 mL of CH2Cl2 at 0° C. was added dropwise a solution of SnCl4 (2.64 g, 10.1 mmol) in 5 mL of CH2Cl2. After 2.5 hours the reaction was quenched by the slow addition of 20 mL H2O. The organic layer was washed with 1M aqueous HCl, 5% aqueous NaOH, H2O, and finally saturated aqueous NaCl before being dried over MgSO4. Concentration under reduced pressure afforded 1.90 g (78%) the title compound as a tan solid. 1H NMR (300 MHz, CDCl3)δ: 7.72 (1H, d, J=8.9 Hz), 6.95 (1H, d, J=11.0 Hz), 3.91 (3H, s), 2.85 (2H, s), 1.47 (6H,s).

Workup

  1. customAfter 2.5 hours the reaction was quenched by the slow addition of 20 mL H2O
  2. washThe organic layer was washed with 1M aqueous HCl, 5% aqueous NaOH, H2O, and finally saturated aqueous NaCl
  3. dry with materialbefore being dried over MgSO4
  4. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-3a73bcc0e7bb4942981a5bfcd2053921
Source dataset
uspto-grants-1999_09
Patent number
US05958954

Reaction notes

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