1-Propanol → HCID 178466787、化合物

HRID 1161176ノート

反応式

HRID 1161176 の反応式
Br[CH2:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([OH:18])[C:10]=2[Cl:19])=[CH:5][CH:4]=1.[OH:22][C:23]1[CH:27]=[C:26]([C:28]2[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=2)[O:25][N:24]=1.C([O-])([O-])=O.[Na+].[Na+].C(O)CC>O.C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:22][C:23]1[CH:27]=[C:26]([C:28]2[CH:33]=[C:32]([CH:31]=[CH:30][CH:29]=2)[CH2:2][C:3]2[CH:21]=[CH:20][C:6]([CH2:7][O:8][C:9]3[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([OH:18])[C:10]=3[Cl:19])=[CH:5][CH:4]=2)[O:25][N:24]=1

参加物

8

反応物 4

HCID 10311-PropanolHCID 10340Sodium CarbonateHCID 574384161-(4-((4-(Bromomethyl)benzyl)oxy)-3-chloro-2-hydroxyphenyl)ethanoneHCID 178514831HCID 178514831、化合物

生成物 1

HCID 178466787HCID 178466787、化合物収率 5.5%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
70 °C

実験手順

Add 1-(4-(4-(bromomethyl)benzyloxy)-3-chloro-2-hydroxyphenyl)ethanone (180 mg, 0.487 mmol) and 3-(3-hydroxyisoxazol-5-yl)phenylboronic acid (218 mg, 1.06 mmol) to a 2.0 M solution of Na2CO3 in water (2.36 mL), dimethoxyethane (4.72 mL), and n-PrOH (4.72 mL). Degas the solution. Add tetrakis(triphenylphosphine)palladium (0) (123 mg, 0.106 mmol) and degas the mixture. Heat the mixture at 70° C. for 12 h. Quench the reaction with water. Extract with EtOAc. Dry, filter and concentrate. Purify the residue by flash chromatography on silica gel afforded the title compound (12 mg, 5%): 1H NMR (d6-DMSO) δ 2.61 (s, 3H), 4.02 (s, 2H), 5.31 (s, 2H), 6.51 (s, 1H), 6.89 (d, J=9.0 Hz, 1H), 7.31-7.36 (m, 3H), 7.39-7.44 (m, 3H), 7.62 (d, J=7.8 Hz, 1H), 7.70 (s, 1H), 7.93 (d, J=9.4 Hz, 1H), 11.34 (s, 1H), 13.13 (s, 1H); MS (APCI-neg mode) m/z (rel intensity): 448 (M−H, 100%).

後処理

  1. customDegas the solution
  2. customQuench
  3. customthe reaction with water
  4. extractionExtract with EtOAc
  5. customDry
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the residue by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-5138a557b545476cabcf4cceb7cfdbf5
出典データセット
uspto-grants-2010_10
特許番号
US07816523B2

反応ノート

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