Phenylboronic Acid → 3,5-Diphenyl-4-[(2-methoxyethoxy)methoxy]-benzaldehyde

HRID 1281434

反応式

HRID 1281434 の反応式
I[C:2]1[CH:3]=[C:4]([CH:7]=[C:8](I)[C:9]=1[O:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:5]=[O:6].[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>COCCOC.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:18]1([C:2]2[CH:3]=[C:4]([CH:7]=[C:8]([C:2]3[CH:3]=[CH:4][CH:7]=[CH:8][CH:9]=3)[C:9]=2[O:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:5]=[O:6])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

6

反応物 2

HCID 66827Phenylboronic AcidHCID 222376563,5-Diiodo-4-(2-methoxyethoxymethoxy)benzaldehyde

生成物 1

HCID 222375093,5-Diphenyl-4-[(2-methoxyethoxy)methoxy]-benzaldehyde収率 155.5%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of 3,5-diiodo-4-(2-methoxyethoxymethyloxy)-benzaldehyde (19.094 g, 41.327 mmol), Pd(OAc)2(0.185 g, 0.02 mmol), phenylboronic acid (11.429 g, 90.920 mmol) and Ba(OH)2.8H2O (39.114 g, 123.981 mmol) in DME (700 ml) and water (110 ml) was refluxed. After 90 minutes, the reaction mixture was cooled, concentrated to about 400 ml and the residue extracted with EtOAc (1×300 ml, 3×100 ml). The combined organics were washed with saturated NaHCO3 (3×75 ml), water (2×75 ml), brine (2×75 ml), dried over Na2SO4, filtered and the filtrate concentrated in vac and dried. The residue was purified by flash chromatography (hexane, 5% and 12% EtOAc/Hex) to give the product as a light yellow viscous oil (11.645 g, 78%); 1H NMR (400 MHz, DMSO-d6) δ 2.79-2.82 (m, 2H), 2.89-2.92 (m, 2H), 3.02 (s, 3H), 4.42 (s, 2H), 7.42-7.46 (m, 2H), 7.48-7.54 (m, 4H), 7.62-7.66 (m, 4H), 7.91 (s, 2H), 10.07 (s, 1H); IR (film) 3050, 2880, 1690,1580 cm−1; mass spectrum [EI], m/z 362 M+.

後処理

  1. temperaturewas refluxed
  2. temperaturethe reaction mixture was cooled
  3. concentrationconcentrated to about 400 ml
  4. extractionthe residue extracted with EtOAc (1×300 ml, 3×100 ml)
  5. washThe combined organics were washed with saturated NaHCO3 (3×75 ml), water (2×75 ml), brine (2×75 ml)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vac
  9. customdried
  10. customThe residue was purified by flash chromatography (hexane, 5% and 12% EtOAc/Hex)

出典と根拠

ORDレコード
ord-6e0dd549a12145f7860ebb90129240b9
出典データセット
uspto-grants-2002_09
特許番号
US06451827B2

関連ノート

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