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

HRID 30390노트

반응식

HRID 30390 반응식
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

참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 69207439HCID 69207439, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-26d715387cc24725a5fff30d1053a4ad
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423067B2

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