Potassium Carbonate → Cyclohexylmethyl 5-chlorothiophene-2-carboxylate

HRID 63300

반응식

HRID 63300 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 84819867Cyclohexylmethyl 5-chlorothiophene-2-carboxylate

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-30c4ccd6c9304edebef711969c425c30
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447078B2

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