Water → HCID 118622763, compound

HRID 2202221Notes

Reaction equation

HRID 2202221 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11]C(OCC)=O)[CH:5]=C(OC)C=1.[CH3:17][Mg]Br.[CH2:20]([O:22][CH2:23][CH3:24])C.O.C([O:29][CH2:30][CH3:31])(=O)C>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:30]([CH3:31])([OH:29])[CH3:17])[CH:5]=[C:23]([O:22][CH3:20])[CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 118622779HCID 118622779, compoundHCID 178467822HCID 178467822, compound

Product 1

HCID 118622763HCID 118622763, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(3-fluoro-5-methoxyphenyl)propanoate (13.9 g, 61.44 mmol) in anhydrous THF (200 mL) was added dropwise 3M methylmagnesium bromide/diethyl ether solution (61.4 mL, 184.31 mmol) at 0° C., and the mixture was stirred at room temperature for 1 hr under nitrogen atmosphere. To the reaction mixture were added water and ethyl acetate, and the organic layer was separated. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give 4-(3-fluoro-5-methoxyphenyl)-2-methylbutan-2-ol (12.1 g, 57.01 mmol, 93%). This compound was used for the next step without purification.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c3cd0ecd985b49c48b133066e232caff
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

Loading…