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

HRID 916032ノート

反応式

HRID 916032 の反応式
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

参加物

4

反応物 2

HCID 20796135HCID 20796135、化合物HCID 21226445Aluminium lithium hydride

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a chilled (0° C.) solution of 400 mg (1.14 mmol) of 3,3,3-trifluoro-2-[1-(5-fluoro-2methoxyphenyl)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, 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.

後処理

  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

出典と根拠

ORDレコード
ord-8abade3c3aa341ef82a4ecf337c046af
出典データセット
uspto-grants-2007_09
特許番号
US07268152B2

反応ノート

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