Cyclohexanemethanol → Cyclohexylmethyl 4-(cyclohexylmethoxy)thiophene-2-carboxylate

HRID 63316

반응식

HRID 63316 반응식
[CH:1]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[C:12]1[CH:13]=[C:14]([C:17]([O:19][CH2:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:18])[S:15][CH:16]=1.[NH4+].[Cl-]>C1COCC1.[Cu]I>[CH:1]1([CH2:7][O:8][C:12]2[CH:13]=[C:14]([C:17]([O:19][CH2:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:18])[S:15][CH:16]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 7507CyclohexanemethanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86694606Cyclohexylmethyl 4-bromothiophene-2-carboxylate

생성물 1

HCID 86694607Cyclohexylmethyl 4-(cyclohexylmethoxy)thiophene-2-carboxylate

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매

실험 절차

Cyclohexylmethanol (0.50 mL, 4.06 mmol) was added to a suspension of NaH (0.080 g, 3.33 mmol) in anhydrous THF (5 mL). Then cyclohexylmethyl 4-bromothiophene-2-carboxylate (0.56 g, 1.847 mmol) was added to the reaction mixture followed by CuI (0.34 g, 1.79 mmol). The reaction mixture was stirred at room temperature for 12 days then aqueous NH4Cl (25%) was added. Aqueous layer was extracted with EtOAc and combined organic layers were washed with brine, dried over anhydrous MgSO4 and concentrated under reduced pressure. Flash chromatography purification (2%-10% EtOAc—hexanes gradient) gave cyclohexylmethyl 4-(cyclohexylmethoxy)thiophene-2-carboxylate as a colorless oil. Yield (0.17 g, 27%); 1H NMR (400 MHz, CD3OD) δ 7.35 (d, J=1.7 Hz, 1H), 6.75 (d, J=1.7 Hz, 1H), 4.07 (d, J=6.3 Hz, 2H), 3.78 (d, J=6.3 Hz, 2H), 1.65-1.90 (m, 12H), 1.15-1.38 (m, 6H), 1.00-1.15 (m, 4H).

후처리

  1. extractionAqueous layer was extracted with EtOAc
  2. washwere washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customFlash chromatography purification (2%-10% EtOAc—hexanes gradient)

출처 및 근거

ORD 기록
ord-198b10e8e72d497abae75e380763bb01
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447078B2

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