Hydrochloric Acid → 5-Biphenyl-4-yl-2-methyl-3-oxo-pentanoic acid tert-butyl ester

HRID 1297257ノート

反応式

HRID 1297257 の反応式
[C:1]([O:5][C:6](=[O:24])[CH2:7][C:8](=[O:23])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:27]I.Cl>CN(C)C=O>[C:1]([O:5][C:6](=[O:24])[CH:7]([CH3:27])[C:8](=[O:23])[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:15][CH:16]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58914664Tert-butyl 5-biphenyl-4-yl-3-oxopentanoate2 回

生成物 1

HCID 586751335-Biphenyl-4-yl-2-methyl-3-oxo-pentanoic acid tert-butyl ester収率 52%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of 5-biphenyl4-yl-3-oxo-pentanoic acid tert-butyl ester (Intermediate 2, 0.30 g, 0.93 mmol) in dimethyl formamide (1.5 mL) was added to a suspension of sodium hydride (60%; 38 mg, 0.94 mmol) in dimethyl formamide (1 mL) at 0° C. under nitrogen. After stirring for 20 minutes methyl iodide (58 μL, 0.93 mmol) was added and the reaction warmed to room temperature at which stirring was continued for 2 hours. 0.5 M Hydrochloric acid (5 mL) was added and the quenched reaction mixture extracted with diethyl ether (3×5 mL). The organic phases were combined, washed with brine (5 mL) and dried (MgSO4). The volatiles were removed by evaporation under reduced pressure and the residue was purified by column chromatography on silica gel (1:6 diethyl ether: 40–60 petroleum ether) to give the title compound (163 mg, 52%) as a colourless oil. LC/MS: 3.81 min; z/e 356, calcd (M+NH4) 356. 1H NMR (400 MHz: CDCl3): 7.59 (2 H), 7.51 (2 H), 7.42 (2 H), 7.32 (1 H), 7.22 (2 H), 3.42 (1 H), 2.97 (3 H), 2.83 (1 H), 1.42 (9 H), 1.28 (3 H).

後処理

  1. additionwas added
  2. customthe quenched reaction mixture
  3. extractionextracted with diethyl ether (3×5 mL)
  4. washwashed with brine (5 mL)
  5. dry with materialdried (MgSO4)
  6. customThe volatiles were removed by evaporation under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (1:6 diethyl ether: 40–60 petroleum ether)

出典と根拠

ORDレコード
ord-1531af86f5334276a7a8a756d45f09e3
出典データセット
uspto-grants-2007_07
特許番号
US07250439B2

反応ノート

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