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Ammonium Chloride → 1-(2'-Fluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-yl)-2,2-dimethyl-1-propanone

HRID 1662417
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HRID 1662417 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:16]([O:18]C)=O)=[CH:10][C:11]([CH2:14][OH:15])=[CH:12][CH:13]=1.[C:20]([Li])([CH3:23])([CH3:22])[CH3:21].[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][C:9]=1[C:16](=[O:18])[C:20]([CH3:23])([CH3:22])[CH3:21]
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참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 57705859Methyl 2'-fluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-carboxylateHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 577068821-(2'-Fluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-yl)-2,2-dimethyl-1-propanone수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 66.32C (0.850 g, 3 mmol) in THF (33 mL) at −78° C. was added tert-butyllithium (6 mL, 10 mmol, 1.7M). The reaction was stirred for 5 hours and then a saturated solution of ammonium chloride was added and the mixture was extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-40% EtOAc in hexanes) to yield 66.32D as a colorless oil (0.670 g, 72% yield).

후처리

  1. extractionthe mixture was extracted three times with EtOAc
  2. dry with materialAfter drying over anhydrous magnesium sulfate
  3. filtrationfiltering
  4. customthe organic solvent was removed under reduced pressure
  5. customthe product was then purified on silica gel (0-40% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-1b8cc68862674530854071c3acf5bd99
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08030354B2

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