Triethylamine → HCID 13170366、化合物

HRID 736860ノート

反応式

HRID 736860 の反応式
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].C(N(CC)CC)C.[Si:32]([O:39][C:40]1[CH:47]=[CH:46][C:43](C=O)=[CH:42][CH:41]=1)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]>ClCCl>[Br:21][C:20]([Br:24])=[CH:1][C:47]1[CH:46]=[CH:43][CH:42]=[CH:41][C:40]=1[O:39][Si:32]([C:35]([CH3:36])([CH3:37])[CH3:38])([CH3:33])[CH3:34]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 108791334-{[tert-Butyl(dimethyl)silyl]oxy}benzaldehyde

生成物 1

HCID 13170366HCID 13170366、化合物収率 107.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Triphenylphosphine (3.44 g, 13.1 mmol) was dissolved in dichloromethane (25 ml) in nitrogen atmosphere, carbon tetrabromide (2.18 g, 6.56 mmol) was added little by little under cooling with ice, and triethylamine (4.4 ml, 26.2 mmol) was dropwise added, followed by stirring for 10 minutes. Then, under cooling with ice, a dichloromethane solution (20 ml) of 4-(tert-butyldimethylsilyloxy)benzaldehyde (10.0 g, 73.4 mmol) prepared in 1) was dropwise added, followed by stirring for 1 hour. Silica gel (50 g) was added to the reaction solution, the reaction solution was concentrated under reduced pressure to dryness, and the resulting product was purified by silica gel column chromatography (hexane:ethyl acetate=20:1, containing 0.1% v/v triethylamine) to give 1,1-dibromo-2-(tert-butyldimethylsilyloxyphenyl)ethylene (2.77 g, 81%) as a pale yellow oily substance.

後処理

  1. additionwas added little by little
  2. additionwas dropwise added
  3. temperatureThen, under cooling with ice
  4. additionwas dropwise added
  5. stirringby stirring for 1 hour
  6. additionSilica gel (50 g) was added to the reaction solution
  7. concentrationthe reaction solution was concentrated under reduced pressure to dryness
  8. customthe resulting product was purified by silica gel column chromatography (hexane
  9. additionethyl acetate=20:1, containing 0.1% v/v triethylamine)

出典と根拠

ORDレコード
ord-48d234ce93d74c7181df844808c40222
出典データセット
uspto-grants-2009_09
特許番号
US07595415B2

反応ノート

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