Ethynylcyclohexane → Cyclohexylmethyl 5-(cyclohexylethynyl)furan-2-carboxylate

HRID 63322

반응식

HRID 63322 반응식
Br[C:2]1[O:6][C:5]([C:7]([O:9][CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:8])=[CH:4][CH:3]=1.[C:17]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)#[CH:18]>CCN(CC)CC.[Cu]I>[CH:19]1([C:17]#[C:18][C:2]2[O:6][C:5]([C:7]([O:9][CH2:10][CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)=[O:8])=[CH:4][CH:3]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

참가 물질

5

반응물 2

HCID 70263EthynylcyclohexaneHCID 86694615Cyclohexylmethyl 5-bromofuran-2-carboxylate

생성물 1

HCID 86694616Cyclohexylmethyl 5-(cyclohexylethynyl)furan-2-carboxylate

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8471Triethylamine용매

실험 절차

A mixture of cyclohexylmethyl 5-bromofuran-2-carboxylate (0.63 g, 2.19 mmol) and ethynylcyclohexane (0.32 g, 2.96 mmol) in Et3N (10 mL) was degassed by bubbling Ar. CuI (0.023 g, 0.119 mmol) and PdCl2(Ph3P)2 (0.0412 g, 0.0587 mmol) were added and the reaction mixture was degassed by alternating vac/Ar three 3 times. The reaction mixture was stirred at +70° C. under Ar overnight and concentrated under reduced pressure. The residue was partitioned between hexanes and aqueous NH4Cl (25%) and aqueous layer was extracted twice with hexanes. Combined organic layers were washed with brine, treated with activated charcoal and dried over anhydrous MgSO4. Concentration under reduced pressure gave cyclohexylmethyl 5-(cyclohexylethynyl)furan-2-carboxylate as an orange solid which was used directly in the next step without additional purification. Yield (0.75 g, quant.); 1H NMR (400 MHz, CDCl3) δ 7.10 (d, J=3.9 Hz, 1H), 6.50 (d, J=3.9 Hz, 1H), 4.10 (d, J=6.4 Hz, 2H), 1.56-2.66 (m, 1H), 1.63-1.84 (m, 9H), 1.42-1.60 (m, 4H), 1.10-1.40 (m, 6H), 0.96-1.10 (m, 2H).

후처리

  1. customwas degassed
  2. customby bubbling Ar
  3. customthe reaction mixture was degassed
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between hexanes and aqueous NH4Cl (25%) and aqueous layer
  6. extractionwas extracted twice with hexanes
  7. washCombined organic layers were washed with brine
  8. additiontreated with activated charcoal
  9. dry with materialdried over anhydrous MgSO4
  10. concentrationConcentration under reduced pressure

출처 및 근거

ORD 기록
ord-ee60ea3880d24478967c8fa9c727501a
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447078B2

연결된 노트

불러오는 중…