Sodium Carbonate → 6-[3-(t-Butyl)-4-methoxyphenyl]-2-naphthaldehyde

HRID 860557노트

반응식

HRID 860557 반응식
[C:1]([C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].Br[C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[C:22]([CH:27]=[O:28])[CH:21]=[CH:20]2.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH:23]=[C:22]([CH:27]=[O:28])[CH:21]=[CH:20]3)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 106321513-Tert-butyl-4-methoxyphenylboronic acidHCID 134770296-Bromonaphthalene-2-carbaldehyde

생성물 1

HCID 865860436-[3-(t-Butyl)-4-methoxyphenyl]-2-naphthaldehyde수율 92.4%

시약·촉매·용매 4

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 21863594Toluene ethanol용매

실험 절차

A mixture of 3-(t-butyl)-4-methoxyphenyl boronic acid (0.424 g, 2.04 mmol), 6-bromo-2-naphthaldehyde (0.400 g, 1.70 mmol) and sodium carbonate (0.541 g, 5.10 mmol) in 10 mL of toluene:ethanol (4:1) and water (1 mL) was degassed with argon for 30 minutes. Tetrakis(triphenylphosphine) palladium(0) (0.059 g, 0.05 mmol) was added and the mixture heated at reflux for 17 hours. The solution was cooled to room temperature, diluted with ethyl acetate and washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (eluent: hexane:EtOAc, 9:1) to give 0.50 g of 6-[3-(t-butyl)-4-methoxyphenyl]-2-naphthaldehyde (76%) as a solid. 1H NMR (300 MHz; DMSO-d6, 300 MHz): 1.46 (s, 9H), 3.92 (s, 3H), 7.02 (d, J=8.7 Hz, 1H), 7.57 (dd, J1=8.7 Hz, J2=2.4 Hz, 1H), 7.66 (d, J=2.4 Hz, 1H), 7.84 (dd, J1=8.4 Hz, J2=1.8 Hz, 1H), 7.97 (brs, 2H), 8.04 (s, 1H), 8.05 (d, J=8.7 Hz, 1H), 8.35 (s, 1H), 10.16 (s, 1H).

후처리

  1. customwas degassed with argon for 30 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux for 17 hours
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on silica gel (eluent: hexane:EtOAc, 9:1)

출처 및 근거

ORD 기록
ord-112492b17dad4e7aa63468d8b3f3dcfc
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153875B2

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