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Aluminium lithium hydride → 1-(2'-Fluoro-4-hydroxymethyl-5'-methoxy-biphenyl-2-yl)-2,2-dimethyl-but-3-en-1-ol

HRID 404383
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HRID 404383 반응식
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])=[C:7]([CH:20]([OH:26])[C:21]([CH3:25])([CH3:24])[CH:22]=[CH2:23])[CH:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:19][C:12]1[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([CH2:3][OH:2])=[CH:6][C:7]=1[CH:20]([OH:26])[C:21]([CH3:25])([CH3:24])[CH:22]=[CH2:23]
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참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 574676322'-Fluoro-2-(1-hydroxy-2,2-dimethyl-but-3-enyl)-5'-methoxy-biphenyl-4-carboxylic acid methyl ester

생성물 1

HCID 574676511-(2'-Fluoro-4-hydroxymethyl-5'-methoxy-biphenyl-2-yl)-2,2-dimethyl-but-3-en-1-ol수율 90.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 21.4 (530 mg, 1479 μmol) in THF (20 mL), was added LAH (168 mg, 4436 μmol). The resulting mixture was stirred at room temperature for 1 hour. The solvent was then removed, and the residue was diluted with EtOAc. The organic layer was washed with 1N NaOH, water, and brine. The organic layer was then dried over sodium sulfate, filtered, and the organic solvent was removed in vacuo to give an oil (442 mg, 90%) which was used without further purification. MS ESI m/e: 331.2 (M+H)+.

후처리

  1. customThe solvent was then removed
  2. additionthe residue was diluted with EtOAc
  3. washThe organic layer was washed with 1N NaOH, water, and brine
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. filtrationfiltered
  6. customthe organic solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-f668ddaed1f64da0b91c7570f2dc6eab
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08748462B2

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