HCID 20796135, compound → 1,1,1-Trifluoro-3-[1-(5-fluoro-2-methoxyphenyl)cyclopropyl]propan-2-one

HRID 2080599Notes

Reaction equation

HRID 2080599 reaction equation
C(OC(=O)[C:5]([CH2:11][C:12]1([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])[CH2:14][CH2:13]1)([OH:10])[C:6]([F:9])([F:8])[F:7])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:9][C:6]([F:7])([F:8])[C:5](=[O:10])[CH2:11][C:12]1([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 20796135HCID 20796135, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 223984731,1,1-Trifluoro-3-[1-(5-fluoro-2-methoxyphenyl)cyclopropyl]propan-2-oneYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a chilled (0° C.) solution of 400 mg (1.14 mmol) of 3,3,3-trifluoro-2-[1-(5-fluoro-2-methoxyphenyl)cyclopropylmethyl]-2-hydroxypropionic acid ethyl ester in 5 mL of anhydrous THF was added 98 mg (2.58 mmol) of lithium aluminum hydride in several portions. The cold bath was then removed and the mixture was stirred at room temperature. After 4.5 hours, the mixture was cooled in an ice water bath and cautiously quenched with water, dried over magnesium sulfate, and filtered through diatomaceous earth, washing with EtOAc to afford 278 mg (78%) of title compound which was used without further purification. The filter cake was partitioned between 15 mL of 1 N aqueous hydrochloric acid and extracted with three 10 mL portions of EtOAc. The combined organic layers were washed with two 10 mL portions of 1 N aqueous hydrochloric acid, 10 mL of brine, and two 10 mL portions of saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated to afford an addition 32 mg (8.9%) of 3,3,3-trifluoro-2-[1-(5-fluoro-2-methoxyphenyl)cyclopropylmethyl]propane-1,2-diol.

Workup

  1. customThe cold bath was then removed
  2. temperaturethe mixture was cooled in an ice water bath
  3. customcautiously quenched with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through diatomaceous earth
  6. washwashing with EtOAc

Sources & evidence

ORD record
ord-124c289f7105443ca26576d8e6c2ae26
Source dataset
uspto-grants-2011_04
Patent number
US07932392B2

Reaction notes

Loading…