Lithium Hexamethyldisilazide → 1-Bromo-5-(4-Cyanophenyl]-4-Pentene

HRID 979775ノート

反応式

HRID 979775 の反応式
[Br-].[C:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:6][CH:5]=1)#[N:3].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Br:40][CH2:41][CH2:42][CH2:43][CH:44]=O>C1COCC1>[Br:40][CH2:41][CH2:42][CH2:43][CH:44]=[CH:10][C:7]1[CH:6]=[CH:5][C:4]([C:2]#[N:3])=[CH:9][CH:8]=1

参加物

5

反応物 3

HCID 2733832Lithium HexamethyldisilazideHCID 2778276(4-Cyanobenzyl)triphenylphosphonium bromideHCID 30160054-Bromobutyraldehyde

生成物 1

HCID 700617381-Bromo-5-(4-Cyanophenyl]-4-Pentene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

Add (4-cyanophenylmethyl)triphenylphosphonium bromide (27.25 g) to dry THF (65 ml) and cool to -20° C. under an argon atmosphere. With stirring, dropwise add 65 ml of a solution of 1 molar lithium bis(trimethylsilyl)amide in THF, maintaining the temperature at -20° C. Stir for 30 minutes at -20° C.; then for 30 minutes at 0° C. Cool to -20° C. and add freshly distilled 4-bromobutanal (10.50 g) dropwise with stirring. Stir at -20° C. for 1 hour, then at room temperature for 16 hours. Remove the solid material by filtration and wash with THF. Vacuum evaporate the solvent from the filtrate and purify the resultant residue by chromatography on silica gel, eluting with CH2Cl2 :hexane(4:1). Combine the desired fractions and vacuum evaporate the solvent to obtain the title compound.

後処理

  1. stirringStir for 30 minutes at -20° C.
  2. temperatureCool to -20° C.
  3. stirringwith stirring
  4. stirringStir at -20° C. for 1 hour
  5. waitat room temperature for 16 hours
  6. customRemove the solid material
  7. filtrationby filtration
  8. washwash with THF
  9. customVacuum evaporate the solvent from the filtrate
  10. custompurify the resultant residue by chromatography on silica gel
  11. washeluting with CH2Cl2 :hexane(4:1)
  12. customCombine the desired fractions and vacuum evaporate the solvent

出典と根拠

ORDレコード
ord-95ec76cba9974f7089f7625cf3e0cc85
出典データセット
uspto-grants-1987_01
特許番号
US04634689

反応ノート

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