Potassium Hydroxide → 1-(3,5-difluorophenyl)cyclopentane-1-carboxylic acid

HRID 30390ノート

反応式

HRID 30390 の反応式
C[O:2][C:3]([C:5]1([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[OH-].[K+]>CS(C)=O.O>[F:16][C:14]1[CH:15]=[C:10]([C:5]2([C:3]([OH:4])=[O:2])[CH2:9][CH2:8][CH2:7][CH2:6]2)[CH:11]=[C:12]([F:17])[CH:13]=1

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 69207439HCID 69207439、化合物

生成物 1

HCID 614968601-(3,5-difluorophenyl)cyclopentane-1-carboxylic acid

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

To a solution of 1-(3,5-difluorophenyl)cyclopentanecarboxylic acid methyl ester (Step A, 2.0 g, 8.3 mmol) in dimethylsulfoxide (5 mL) was added potassium hydroxide (1.9 g, 33 mol) in 2 mL of water. After stirring at room temperature for 2.5 h, the reaction mixture was partitioned between ether (50 mL) and saturated aqueous hydrochloric acid (2 N, 50 mL). The organic layer was separated and the aqueous layer extracted with ether (2×50 mL). The combined extracts were dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to give the title compound. 1H NMR (400 MHz, CD3OD): δ 6.97 (m, 2H), 6.80 (m. 1H), 2.60 (m, 2H), 1.84 (m, 2H), 1.74 (m, 4H).

後処理

  1. customthe reaction mixture was partitioned between ether (50 mL) and saturated aqueous hydrochloric acid (2 N, 50 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with ether (2×50 mL)
  4. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-26d715387cc24725a5fff30d1053a4ad
出典データセット
uspto-grants-2008_09
特許番号
US07423067B2

反応ノート

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