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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
ノート
印刷プレビュー

反応式

HRID 404383 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-f668ddaed1f64da0b91c7570f2dc6eab
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08748462B2

反応ノート

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