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

HRID 1994324

反応式

HRID 1994324 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-55e725f54c8243afb309dfb2588cceec
出典データセット
uspto-grants-2010_01
特許番号
US07652144B2

関連ノート

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