Toluene → alpha-Cyano-3-phenoxybenzyl (1R,trans)-2,2-dimethyl-3-((cyclopropylmethoxyimino)methyl)cyclopropanecarboxylate

HRID 2057586노트

반응식

HRID 2057586 반응식
[CH3:1][C:2]1([CH3:15])[C@H:4]([CH:5]=[N:6][O:7][CH2:8][CH:9]2[CH2:11][CH2:10]2)[C@H:3]1[C:12]([OH:14])=[O:13].[C:16]([CH:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1)#[N:17].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[CH3:1][C:2]1([CH3:15])[C@H:4]([CH:5]=[N:6][O:7][CH2:8][CH:9]2[CH2:10][CH2:11]2)[C@H:3]1[C:12]([O:14][CH:18]([C:16]#[N:17])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:20]=1)=[O:13]

참가 물질

8

반응물 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 12713810alpha-Cyano-3-phenoxybenzyl bromideHCID 53706710(1R,trans)-2,2-dimethyl-3-((cyclopropylmethoxyimino)methyl)cyclopropanecarboxylic acid

생성물 1

HCID 86737089alpha-Cyano-3-phenoxybenzyl (1R,trans)-2,2-dimethyl-3-((cyclopropylmethoxyimino)methyl)cyclopropanecarboxylate수율 80.8%

시약·촉매·용매 3

HCID 66133Benzyl triethylammonium chloride촉매HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매

실험 절차

A mixture of 1.8 g of (1R,trans)-2,2-dimethyl-3-((cyclopropylmethoxyimino)methyl)cyclopropanecarboxylic acid, 2.30 g of α-cyano-3-phenoxybenzyl bromide, 0.05 g of tetrabutylammonium hydrogen sulfate, 0.05 g of benzyltriethylammonium chloride, 0.58 g of potassium carbonate, 10 ml of toluene and 6 ml of water was heated at 60°-70° for 4 hours, let stand overnight at room temperature and reheated at 60°-70° for an additional eight hours. The resulting reaction mixture separated into layers. The toluene layer was separated, washed with water, then with saturated sodium bicarbonate and saturated sodium chloride, dried over magnesium sulfate and stripped to give an oil. This oil was chromatographed on silica gel with a mixture of ether-pentane (1:4 ratio) as the eluant to give 2.7 g of desired product as a yellow oil, [α]D25 --16.2, (CHCl3 ; c=0.02 g/cc).

후처리

  1. temperaturewas heated at 60°-70° for 4 hours
  2. waitreheated at 60°-70° for an additional eight hours
  3. customThe resulting reaction mixture
  4. customseparated into layers
  5. customThe toluene layer was separated
  6. washwashed with water
  7. dry with materialwith saturated sodium bicarbonate and saturated sodium chloride, dried over magnesium sulfate
  8. customto give an oil
  9. customThis oil was chromatographed on silica gel with a mixture of ether-pentane (1:4 ratio) as the eluant

출처 및 근거

ORD 기록
ord-28767e258a3b42a3aa277569dd1d16d9
출처 데이터셋
uspto-grants-1980_07
특허 번호
US04211792

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