Sodium Hydroxide → (1S,1aR,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylic acid

HRID 606354노트

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HRID 606354 반응식
Br[CH2:2][C@H:3]1[C@@H:13]2[C@H:4]1[C:5](=[O:16])[O:6][C:7]1[C:8]([F:15])=[CH:9][CH:10]=[C:11]([F:14])[C:12]=12.[OH-:17].[Na+]>O>[F:15][C:8]1[C:7]2[O:17][CH2:2][C@H:3]3[C@@H:4]([C:5]([OH:16])=[O:6])[C@H:13]3[C:12]=2[C:11]([F:14])=[CH:10][CH:9]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 67047808(1S,1aR,7bS)-1-(bromomethyl)-4,7-difluoro-1a,7b-dihydrocyclopropa[c]chromene-2(1H)-one

생성물 1

HCID 21304923(1S,1aR,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylic acid수율 66.3%

시약·촉매·용매 1

HCID 962Water용매

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온도
90 °C

실험 절차

(1S,1aR,7bS)-1-(bromomethyl)-4,7-difluoro-1a,7b-dihydrocyclopropa[c]chromen-2(1H)-one (360 mg, 1.2 mmol) was mixed with the solution of NaOH (0.1 g, 2.5 mmol) in 5 ml of water and heated at stirring for 1 h at 90° C. After completion the reaction mixture was cooled down and extracted into diethyl ether (2×20 ml). Water phase was acidified with conc. HCl. The precipitate formed was collected by filtration to give 180 mg of pure product. Mother liquor was extracted into ether and washed with brine, dried over magnesium sulfate. Concentration gave additional 70 mg of product (containing up to 15% of impurities). Overall yield about 92%.

후처리

  1. temperatureheated
  2. temperatureAfter completion the reaction mixture was cooled down
  3. extractionextracted into diethyl ether (2×20 ml)
  4. customThe precipitate formed
  5. filtrationwas collected by filtration

출처 및 근거

ORD 기록
ord-a0b6271f83e94565b5ad8b99aeefbd56
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915295B2

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