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

HRID 2084341ノート

反応式

HRID 2084341 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

(1S,1 aR,7bS)-1-(bromomethyl)-4,7-difluoro-1 a,7b-dihydrocyclopropa[c]chromen-2(1 h)-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%.

後処理

  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

出典と根拠

ORDレコード
ord-d2ffb9cb805543598c0149978dbad545
出典データセット
uspto-grants-2004_04
特許番号
US06716850B2

反応ノート

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