Triethylamine → HCID 13170366, 화합물

HRID 736860노트

반응식

HRID 736860 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 13170366HCID 13170366, 화합물수율 107.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-48d234ce93d74c7181df844808c40222
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595415B2

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