Water → 5,7-Difluoro-4-methyl-3,4-dihydro-2H-chromen-4-ol

HRID 561495Notes

Reaction equation

HRID 561495 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:13])[CH2:5][CH2:6][O:7]2.[CH3:14][Mg]Br.O>C(OCC)C>[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([CH3:14])([OH:13])[CH2:5][CH2:6][O:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 468354275,7-Difluorochroman-4-oneHCID 178418573HCID 178418573, compound

Product 1

HCID 583921705,7-Difluoro-4-methyl-3,4-dihydro-2H-chromen-4-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

2.00 g (10.86 mmol) of the compound from Example 170A were dissolved in 40 ml of diethyl ether at 0° C., and 5.4 ml (16.29 mmol) of a 3N solution of methylmagnesium bromide in diethyl ether were slowly added dropwise. Stirring at 0° C. for 1 h was followed by warming to RT, addition of water and diethyl ether to the reaction solution and separation of the phases. The aqueous phase was extracted with diethyl ether, and the combined organic phases were dried over sodium sulfate and filtered, and the solvents were removed in vacuo. The crude product was purified by flash chromatography on silica gel (mobile phase: dichloromethane). 2.03 g (93% of theory) of the title compound were obtained.

Workup

  1. temperatureby warming to RT
  2. customto the reaction solution and separation of the phases
  3. extractionThe aqueous phase was extracted with diethyl ether
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvents were removed in vacuo
  7. customThe crude product was purified by flash chromatography on silica gel (mobile phase: dichloromethane)

Sources & evidence

ORD record
ord-694613f9486e42caa295f72a8f153267
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…