tert-Butyl acrylate → (E)-tert-Butyl 3-(2-(2-ethoxy-2-oxoethyl)phenyl)acrylate

HRID 716009노트

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HRID 716009 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[C:14]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:17])[CH:15]=[CH2:16].C1(C(N)C2CCCCC2)CCCCC1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1/[CH:16]=[CH:15]/[C:14]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:13]

참가 물질

8

반응물 4

HCID 15458tert-Butyl acrylateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2780092Ethyl 2-(2-bromophenyl)acetateHCID 10774245alpha-Cyclohexylcyclohexanemethanamine

생성물 1

HCID 86647801(E)-tert-Butyl 3-(2-(2-ethoxy-2-oxoethyl)phenyl)acrylate

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
70 °C

실험 절차

To a mixture of ethyl 2-(2-bromophenyl)acetate (0.97 g, 4 mmol), t-butyl acrylate (0.51 g, 4 mmol), tris(dibenzylideneacetone)dipalladium(0) (91 mg, 0.1 mmol), dicyclohexylmethylamine (0.98 g, 5 mmol) in dioxane (5 mL) was added tri-tert-butylphosphine (0.2 mL, 1 N in toluene, 0.2 mmol). The mixture was heated at 70° C. for 30 minutes under N2. Ethyl acetate was added, and the mixture was filtered through diatomaceous earth. The filtrate was concentrated and purified by silica gel column chromatography eluting with hexanes and ethyl acetate (10:1) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.79 (m, 1H), 7.72 (d, J=15.6 Hz, 1H), 7.34 (m, 3H), 6.40 (d, J=15.7 Hz, 1H), 4.06 (q, J=7.2 Hz, 2H), 3.84 (s, 2H), 1.48 (s, 9H), and 1.17 (t, J=2 Hz, 3H).

후처리

  1. filtrationthe mixture was filtered through diatomaceous earth
  2. concentrationThe filtrate was concentrated
  3. custompurified by silica gel column chromatography
  4. washeluting with hexanes and ethyl acetate (10:1)

출처 및 근거

ORD 기록
ord-0c4be9da58504281b6d0eeecc0498791
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187483B2

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