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Tributylstannane → 2-(3-Hydroxycyclohexyl)isoindoline-1,3-dione

HRID 2280724
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HRID 2280724 반응식
C([SnH](CCCC)CCCC)CCC.Br[CH:15]1[CH:20]([OH:21])[CH2:19][CH2:18][CH2:17][CH:16]1[N:22]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:32].N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1.CO>[OH:21][CH:20]1[CH2:19][CH2:18][CH2:17][CH:16]([N:22]2[C:23](=[O:32])[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]2=[O:31])[CH2:15]1
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참가 물질

6

반응물 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 143399982-(2-Bromo-3-hydroxy-cyclohexyl)-isoindole-1,3-dione

생성물 1

HCID 41897092-(3-Hydroxycyclohexyl)isoindoline-1,3-dione수율 79.7%

시약·촉매·용매 2

HCID 887Methanol용매HCID 1140
Toluene
용매

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온도
80 °C

실험 절차

Tri-n-butyltin hydride (430 g, 1.48 mol) was added to a stirred solution of 2-(2-bromo-3-hydroxy-cyclohexyl)-isoindole-1,3-dione (400 g, 1.23 mol) and 2,2′-azobis(2-methylpropionitrile) (20 g) in toluene (4000 mL) and methanol (400 mL) and the reaction mixture was stirred at 80° C. for 64 h. The reaction mixture was concentrated to give the crude product. The crude product was washed with petroleum ether and ethyl acetate (1:1) to give 2-(3-hydroxy-cyclohexyl)-isoindole-1,3-dione (240 g, 0.98 mol) as a white solid. 1H NMR (CD3OD, 400 MHz): δ ppm 7.82 (m, 4H), 4.16 (m, 1H), 3.63 (m, 1H), 2.13 (m, 2H), 1.98 (d, 2H), 1.89 (m, 1H),1.68 (t, 1H), 1.46 (m, 1H),1.31 (m, 1H).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customto give the crude product
  3. washThe crude product was washed with petroleum ether and ethyl acetate (1:1)

출처 및 근거

ORD 기록
ord-af7a7f7d828241e9adf130d520d55cbf
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09139534B2

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