Toluene → Ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3,4-dimethylnaphthalen-2-yl)acetate

HRID 514123노트

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HRID 514123 반응식
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[C:4]([CH:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:3]=1[CH3:30].[CH3:31]B1OB(C)OB(C)O1.C([O-])([O-])=O.[K+].[K+].C1(C)C=CC=CC=1>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CCO>[C:26]([O:25][CH:19]([C:4]1[C:3]([CH3:30])=[C:2]([CH3:31])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21])([CH3:28])([CH3:27])[CH3:29]

참가 물질

8

반응물 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 67126305Ethyl 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

생성물 1

HCID 67126302Ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3,4-dimethylnaphthalen-2-yl)acetate

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 702Ethanol용매HCID 962Water용매2회

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온도
100 °C

실험 절차

A suspension of ethyl 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate (25 mg, 51 μmol), trimethylboroxine (21 μL, 0.153 mmol), PdCl2(dppf) (3.7 mg, 5.1 μmol), K2CO3 (70 mg, 0.510 mmol), PhMe (500 μL), EtOH (absolute, 250 μL), and H2O (250 μL) was stirred in a sealed vessel at 100° C. for 3 h. The reaction was cooled to 23° C., diluted with H2O and extracted with EtOAc (3×). Combined organic phases were dried (Na2SO4), filtered, and concentrated, giving crude product. (Yield was not found). 1H NMR (400 MHz, CD3OD) δ 8.08 (d, J=8.2 Hz, 1H), 7.48-7.44 (m, 3H), 7.29-7.26 (m, 4H), 5.15 (s, 1H), 4.20-4.12 (m, 2H), 2.65 (s, 3H), 2.55 (s, 3H), 1.21 (t, J=7 Hz, 3H), 1.00 (s, 9H).

후처리

  1. temperatureThe reaction was cooled to 23° C.
  2. extractionextracted with EtOAc (3×)
  3. dry with materialCombined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customgiving crude product
  7. custom(Yield

출처 및 근거

ORD 기록
ord-eb50a7aa1d1e4756b1f980f0a877f447
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102614B2

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