Tetramethyltin → HCID 21990863、化合物

HRID 7891

反応式

HRID 7891 の反応式
Br[C:2]1[C:10]([O:11][CH3:12])=[C:9]([F:13])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH2:15][CH2:16][CH2:17][CH3:18])[C:6]2=[O:14].[CH3:19][Sn](C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Li+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C)C=O>[CH2:15]([CH:5]1[CH2:4][C:3]2[C:7](=[CH:8][C:9]([F:13])=[C:10]([O:11][CH3:12])[C:2]=2[CH3:19])[C:6]1=[O:14])[CH2:16][CH2:17][CH3:18]

参加物

7

反応物 4

HCID 11661TetramethyltinHCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 21990906HCID 21990906、化合物

生成物 1

HCID 21990863HCID 21990863、化合物収率 24.5%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-bromo-2-butyl-6-fluoro-5-methoxy-1-indanone (1.86 g, 5.94 mmol), bis(triphenylphosphine)palladium(II) chloride (208 mg, 0.297 mmol), tetramethyltin (0.989 mL, 7.128 mmol), triphenylphosphine (156 mg, 0.594 mmol), lithium chloride (504 mg, 11.88 mmol), and anhydrous N,N-dimethyl-formamide (11.9 mL) was placed under a nitrogen atmosphere, stirred, and heated in an oil bath at 100° C. for 22 hours. After cooling to room temperature, the mixture was evaporated under vacuum. The residue in EtOAc (150 mL) was washed with water (4×100 mL) and brine (50 mL), dried over MgSO4, filtered, and evaporated under vacuum to an oil (2.15 g). The crude product was purified by chromatography on EM silica gel 60 (2.5×29 cm column), eluting with CH2Cl2 (50 mL fore-run followed by 8 mL fractions). Fractions 20-28 were combined and evaporated under vacuum to provide 2-butyl-6-fluoro-5-methoxy-4-methyl-1-indanone (365 mg) as an oil.

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was evaporated under vacuum
  3. washThe residue in EtOAc (150 mL) was washed with water (4×100 mL) and brine (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum to an oil (2.15 g)
  7. customThe crude product was purified by chromatography on EM silica gel 60 (2.5×29 cm column)
  8. washeluting with CH2Cl2 (50 mL fore-run followed by 8 mL fractions)
  9. customevaporated under vacuum

出典と根拠

ORDレコード
ord-270913168eb241f99a23be25455ccdcc
出典データセット
uspto-grants-2006_08
特許番号
US07087599B2

関連ノート

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