Dimethylformamide → 3-Cyclopentyloxy-6-fluoro-4-methoxybenzaldehyde

HRID 1825382

反応式

HRID 1825382 の反応式
[F:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([OH:10])=[C:4]([O:11][CH3:12])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH:24]1(Br)[CH2:28][CH2:27][CH2:26][CH2:25]1>O>[CH:24]1([O:10][C:5]2[CH:6]=[C:7]([C:2]([F:1])=[CH:3][C:4]=2[O:11][CH3:12])[CH:8]=[O:9])[CH2:28][CH2:27][CH2:26][CH2:25]1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 5981462-Fluoro-5-hydroxy-4-methoxybenzaldehyde

生成物 1

HCID 221457953-Cyclopentyloxy-6-fluoro-4-methoxybenzaldehyde

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 6-fluoro-3-hydroxy-4-methoxybenzaldehyde (2 g), potassium carbonate (1.66 g) and anhydrous dimethylformamide (20 mL) is treated with cyclopentyl bromide (1.62 mL) and heated on a steam bath for 43 hours. The mixture is cooled, poured into water (200 mL) and extracted with diethyl ether (3×100 mL). The combined ethereal extracts are washed with sodium hydroxide solution (2×50 mL; 2 N), and brine (2×50 mL), dried over magnesium sulphate and concentrated. The residual brown oil is subjected to flash chromatography [a solvent gradient of 9:1 to 4:1 v/v petroleum ether (b.p. 60–80° C.) and ethyl acetate is used as eluent on a silica gel column] to give 3-cyclopentyloxy-6-fluoro-4-methoxybenzaldehyde (1.42 g) in the form of a yellow oil. [NMR (CDCl3):—10.22(s,1H),7.27(d,1H,J=8 Hz),6.63(d,1H,J=16 Hz), 4.81–4.76(m,1H),3.91(s,3H),2.01–1.57(m,8H)].

後処理

  1. temperatureheated on a steam bath for 43 hours
  2. temperatureThe mixture is cooled
  3. extractionextracted with diethyl ether (3×100 mL)
  4. washThe combined ethereal extracts are washed with sodium hydroxide solution (2×50 mL; 2 N), and brine (2×50 mL)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-3f88a733e92e42a0adb58ede9894834d
出典データセット
uspto-grants-2006_05
特許番号
US07045660B2

関連ノート

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