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Triphenylphosphine → Ethyl 4'-(4-chlorobutoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate

HRID 253495
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HRID 253495 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:19]1[CH:28]=[CH:27][C:26]2[C:25]([CH3:30])([CH3:29])[CH2:24][CH2:23][C:22]([CH3:32])([CH3:31])[C:21]=2[CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl:66][CH2:67][CH2:68][CH2:69][CH2:70]O>O1CCCC1.O>[Cl:66][CH2:67][CH2:68][CH2:69][CH2:70][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:13]=2)=[CH:4][C:3]=1[C:19]1[CH:28]=[CH:27][C:26]2[C:25]([CH3:30])([CH3:29])[CH2:24][CH2:23][C:22]([CH3:31])([CH3:32])[C:21]=2[CH:20]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 135694-Chloro-1-butanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 57552328Ethyl 4'-hydroxy-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate

생성물 1

HCID 66856889Ethyl 4'-(4-chlorobutoxy)-3'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate수율 74.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

10 g (23 mmol) of ethyl 4′-hydroxy-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate are dissolved in 400 ml of tetrahydrofuran. 9.2 g (35 mmol) of triphenylphosphine and 6.9 ml (35 mmol) of diisopropyl azodicarboxylate are added and the reaction medium is stirred at room temperature for 30 minutes. 2.8 ml (28 mmol) of 4-chlorobutanol are then added, and the medium is kept stirring for 12 hours, and then poured into 500 ml of water and extracted with ethyl acetate. The residue obtained is purified by chromatography on silica gel (eluent: 80/20 heptane/ethyl acetate). 8.9 g of ethyl 4′-(4-chlorobutoxy)-3′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)biphenyl-4-carboxylate are obtained in the form of a colorless oil (yield=73%).

후처리

  1. stirringthe medium is kept stirring for 12 hours
  2. extractionextracted with ethyl acetate
  3. customThe residue obtained
  4. customis purified by chromatography on silica gel (eluent: 80/20 heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-d9828bce845d42579e1a48b8a3b4058d
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07872026B2

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