Carbon Dioxide → 3-{4-[(3-Fluorophenyl)methoxy]phenyl}prop-2-ynoic acid

HRID 2184354노트

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HRID 2184354 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[CH:14])=[CH:9][CH:8]=1.C([Li])CCC.[C:23](=[O:25])=[O:24].Cl>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:23]([OH:25])=[O:24])=[CH:9][CH:8]=1

참가 물질

7

반응물 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 224766251-[(4-Ethynylphenoxy)methyl]-3-fluorobenzeneHCID 178418339Butyllithium

생성물 1

HCID 692917433-{4-[(3-Fluorophenyl)methoxy]phenyl}prop-2-ynoic acid수율 68%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

1.93 g (8.5 mmol) of 1-(3-fluoro-benzyloxy)-4-ethynyl-benzene is dissolved in 30 ml THF and cooled to −78° C. 5.8 ml (9.4 mmol) of a 1.6 molar solution of n-butyl lithium is slowly added under stirring. The resulting solution is stirred at −78° C. for 30 minutes. An excess of solid carbon dioxide is added and the suspension is slowly allowed to warm to RT. Water is added and the mixture is acidified by addition of aqueous 0.1 molar hydrochloric acid. Extraction with ethyl acetate yields a semi-solid residue which is triturated in diethyl ether to give 1.58 g (68%) of a colorless solid. MS (neg.ions): m/e=269.1 (M−H).

후처리

  1. stirringThe resulting solution is stirred at −78° C. for 30 minutes
  2. temperatureto warm to RT
  3. extractionExtraction with ethyl acetate
  4. customyields a semi-solid residue which
  5. customis triturated in diethyl ether

출처 및 근거

ORD 기록
ord-5e595702ed7b4b95a6f0abd523e25241
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900354B2

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