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

HRID 514123ノート

反応式

HRID 514123 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 702Ethanol溶媒HCID 962Water溶媒2 回

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-eb50a7aa1d1e4756b1f980f0a877f447
出典データセット
uspto-grants-2015_08
特許番号
US09102614B2

反応ノート

読み込み中…