Acetic Anhydride → (Z)-3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(5-(3-chloro-4,4,4-trifluoro-2-butenyloxy)pentyloxy)benzene

HRID 369660

반응식

HRID 369660 반응식
[Cl:1][C:2]1[CH:17]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:23])[Cl:22])[CH:15]=[C:14]([Cl:24])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH:12]=O.[Cl:25][C:26](Cl)(Cl)[C:27]([F:30])([F:29])[F:28].C(OC(=O)C)(=O)C>[Zn].CN(C)C=O>[Cl:24][C:14]1[CH:15]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:22])[Cl:23])[CH:17]=[C:2]([Cl:1])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11]/[CH:12]=[C:26](\[Cl:25])/[C:27]([F:30])([F:29])[F:28]

참가 물질

6

반응물 3

HCID 7918Acetic AnhydrideHCID 96351,1,1-Trichloro-2,2,2-trifluoroethaneHCID 540452085-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetaldehyde

생성물 1

HCID 86755966(Z)-3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(5-(3-chloro-4,4,4-trifluoro-2-butenyloxy)pentyloxy)benzene수율 14%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 1.21 g of 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetaldehyde, 0.57 g of zinc dust and 10 ml of N,N-dimethylformamide was added 0.82 g of 1,1,1-trichlorotrifluoroethane. After stirring at room temperature for 1.5 hours, 0.44 g of acetic anhydride was added. The reaction mixture was stirred at room temperature for 3 hours and then filtered. The filtrate was poured into 20 ml of diluted hydrochloric acid and extracted twice with 50 ml of diethyl ether. The diethyl ether layers were combined, washed with water, dried over magnesium sulfate and then evaporated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.21 g of (Z)-3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(5-(3-chloro-4,4,4-trifluoro-2-butenyloxy)pentyloxy)benzene [the integrated CF3 signal ratio of Z/E=94/6 as determined by 19F-NMR (CDCl3 /CFCl3)] (yield, 14%), nD26.5 1.5123.

후처리

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours
  2. filtrationfiltered
  3. additionThe filtrate was poured into 20 ml of diluted hydrochloric acid
  4. extractionextracted twice with 50 ml of diethyl ether
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customto give a crude product

출처 및 근거

ORD 기록
ord-ea00d6a1397d483481fa7f3186c5f968
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140274

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