Tetramethyltin → 2-Butyl-5-methoxy-4-methyl-1-indanone

HRID 7846

反応式

HRID 7846 の反応式
Br[C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH2:14][CH2:15][CH2:16][CH3:17])[C:6]2=[O:13].[Li+].[Cl-].[CH:20]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Sn](C)(C)(C)C>CN(C)C=O.O.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>[CH2:14]([CH:5]1[CH2:4][C:3]2[C:7](=[CH:8][CH:9]=[C:10]([O:11][CH3:12])[C:2]=2[CH3:20])[C:6]1=[O:13])[CH2:15][CH2:16][CH3:17]

参加物

8

反応物 4

HCID 11661TetramethyltinHCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 219909024-Bromo-2-butyl-5-methoxy-1-indanone

生成物 1

HCID 219908832-Butyl-5-methoxy-4-methyl-1-indanone収率 496.7%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A solution of 4-bromo-2-butyl-5-methoxy-1-indanone (1.159 g, 3.90 mmol) in anhydrous dimethylformamide (39 mL) was treated with LiCl (455 mg, 10.73 mmol), PPh3 (205 mg, 0.78 mmol), PdCl2(PPh3)2 (205 mg, 0.292 mmol) and Me4Sn (1.08 mL, 7.80 mmol). The mixture was placed under a nitrogen atmosphere, then stirred and heated in an oil bath at 100° C. for 16.5 hours. After cooling to room temperature, the mixture was diluted with water (100 mL) and extracted with Et2O (100 mL, 2×25 mL). The ether extracts were washed with brine, dried over MgSO4, filtered and evaporated under vacuum to a yellow solid (1.29 g). This material was purified by chromatography on EM silica gel 60 (230-400 mesh, 130 mL dry, packed under CH2Cl2), using CH2Cl2 as eluting solvent, to afford a 92:3:5 mixture (0.90 g) of 2-butyl-5-methoxy-4-methyl-1-indanone, the 6-methyl isomer, and the desmethyl product. This material was used as is in the next step.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with Et2O (100 mL, 2×25 mL)
  3. washThe ether extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum to a yellow solid (1.29 g)
  7. customThis material was purified by chromatography on EM silica gel 60 (230-400 mesh, 130 mL dry, packed under CH2Cl2)
  8. washas eluting solvent

出典と根拠

ORDレコード
ord-16948c22a2304cf0b6f9a96bed7293bb
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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