4-bromo-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one → 4-Benzyl-9a-butyl-7-methoxy-1,2,9,9a-tetrahydrofluoren-3-one

HRID 7836

反応式

HRID 7836 の反応式
Br[C:2]1[C:3](=[O:21])[CH2:4][CH2:5][C:6]2([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]=1[C:13]1[C:8](=[CH:9][C:10]([O:15][CH3:16])=[CH:11][CH:12]=1)[CH2:7]2.[CH2:22]([Sn]12CCCN(CCC1)CCC2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:22]([C:2]1[C:3](=[O:21])[CH2:4][CH2:5][C:6]2([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]=1[C:13]1[C:8](=[CH:9][C:10]([O:15][CH3:16])=[CH:11][CH:12]=1)[CH2:7]2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

5

反応物 2

HCID 219909314-bromo-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-oneHCID 219909325-Benzyl-1-aza-5-stanna-bicyclo[3.3.3]undecane

生成物 1

HCID 219909054-Benzyl-9a-butyl-7-methoxy-1,2,9,9a-tetrahydrofluoren-3-one収率 95%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-bromo-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (29.6 mg, 0.0847 mmol), 5-benzyl-1-aza-5-stanna-bicyclo[3.3.3]undecane (38.5 mg, 85% weight pure, 0.0935 mmol), and Pd(PPh3)4 (9.8 mg, 0.00848 mmol) in anhydrous toluene (1.3 mL) was degassed, placed under a nitrogen atmosphere, stirred, and heated in an oil bath at 100° C. After heating 4 hours, the cloudy, dark brown reaction mixture was cooled in an ice bath and filtered through a pad of celite. The filtrate was evaporated under vacuum to an orange gum (57 mg). The crude product was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate, using 9:1 hexanes-EtOAc as developing solvent. The major UV visible band at Rf 0.18-0.26 was removed and eluted with EtOAc to afford 4-benzyl-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (29 mg) as a pale yellow gum.

後処理

  1. customwas degassed
  2. temperatureAfter heating 4 hours
  3. temperaturethe cloudy, dark brown reaction mixture was cooled in an ice bath
  4. filtrationfiltered through a pad of celite
  5. customThe filtrate was evaporated under vacuum to an orange gum (57 mg)
  6. customThe crude product was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate
  7. customThe major UV visible band at Rf 0.18-0.26 was removed
  8. washeluted with EtOAc

出典と根拠

ORDレコード
ord-38f635a0ee364faa8595c22f5d4de8f8
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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