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Sodium Bicarbonate → Rac-6-[(4-tert-butylphenyl)(hydroxy)methyl]-5-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one

HRID 1516700
ノート
印刷プレビュー

反応式

HRID 1516700 の反応式
Br[Mg][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:5][CH:4]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:29]([CH:30]=[O:31])=[C:28]([CH:32]([CH3:34])[CH3:33])[CH:27]=[C:26]3[C:21]=2[C:22](=[O:37])[CH2:23][C:24]([CH3:36])([CH3:35])[O:25]3)=[CH:16][CH:15]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:9]([C:6]1[CH:7]=[CH:8][C:3]([CH:30]([OH:31])[C:29]2[C:20]([C:17]3[CH:16]=[CH:15][C:14]([F:13])=[CH:19][CH:18]=3)=[C:21]3[C:26](=[CH:27][C:28]=2[CH:32]([CH3:34])[CH3:33])[O:25][C:24]([CH3:35])([CH3:36])[CH2:23][C:22]3=[O:37])=[CH:4][CH:5]=1)([CH3:12])([CH3:11])[CH3:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 580030235-(4-Fluorophenyl)-7-isopropyl-2,2-dimethyl-4-oxochroman-6-carbaldehydeHCID 178440986HCID 178440986、化合物

生成物 1

HCID 58002954Rac-6-[(4-tert-butylphenyl)(hydroxy)methyl]-5-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒
2 回

実験手順

At −78° C., 2.12 ml (1.06 mmol) of a freshly prepared 0.5 M solution of bromo(4-tert-butylphenyl)magnesium in tetrahydrofuran are slowly added dropwise to a solution of 300 mg (880 μmol) of 5-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-4-oxochroman-6-carbaldehyde (Example 20A) in 7 ml of tetrahydrofuran. The mixture is then allowed to thaw slowly to −20° C. and stirred at this temperature for 45 min. 10% strength sodium bicarbonate solution is then added, the mixture is extracted three times with ethyl acetate and the combined organic phases are washed with saturated sodium chloride solution. The organic phases are dried over magnesium sulfate, the solvent is then removed under reduced pressure and the residue is purified by column chromatography on silica gel (mobile phase: gradient cyclohexane→cyclohexane/ethyl acetate 10:1).

後処理

  1. customthaw slowly to −20° C.
  2. extractionthe mixture is extracted three times with ethyl acetate
  3. washthe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialThe organic phases are dried over magnesium sulfate
  5. customthe solvent is then removed under reduced pressure
  6. customthe residue is purified by column chromatography on silica gel (mobile phase: gradient cyclohexane→cyclohexane/ethyl acetate 10:1)

出典と根拠

ORDレコード
ord-7ff54fda94f84d70b9249d20bb954d14
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08227511B2

反応ノート

読み込み中…

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