Potassium Carbonate → Cyclohexylmethyl 5-chlorothiophene-2-carboxylate

HRID 63300

反応式

HRID 63300 の反応式
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[CH:10]1([CH2:16]Br)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:1][C:2]1[S:6][C:5]([C:7]([O:9][CH2:16][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 137636Cyclohexane, (bromomethyl)-

生成物 1

HCID 84819867Cyclohexylmethyl 5-chlorothiophene-2-carboxylate

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 5-chlorothiophene-2-carboxylic acid (3.01 g, 19.0 mmol), cyclohexylmethyl bromide (3.51 g, 19.8 mmol) and potassium carbonate (2.81 g, 20.33 mmol) was stirred under Ar at +85° C. for 3 days and cooled to room temperature. Reaction mixture was diluted with water and extracted with hexanes three times. Combined organic layers were dried over anhydrous MgSO4 and concentrated under reduced pressure. Purification by flash chromatography (2%-15% EtOAc—hexanes gradient) gave cyclohexylmethyl 5-chlorothiophene-2-carboxylate as a colorless oil. Yield (4.76 g, 97%); 1H NMR (400 MHz, CDCl3) δ 7.56-7.60 (m, 1H), 6.90-6.94 (m, 1H), 4.08 (d, J=6.10 Hz, 2H), 1.64-1.82 (m, 6H), 1.10-1.34 (m, 3H), 0.97-1.10 (m, 2H).

後処理

  1. customReaction mixture
  2. extractionextracted with hexanes three times
  3. dry with materialCombined organic layers were dried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (2%-15% EtOAc—hexanes gradient)

出典と根拠

ORDレコード
ord-30c4ccd6c9304edebef711969c425c30
出典データセット
uspto-grants-2016_09
特許番号
US09447078B2

関連ノート

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