Potassium Hydroxide → Ethyl 2-[3-(3-bromophenyl)oxetan-3-yl]acetate

HRID 384077노트

반응식

HRID 384077 반응식
[OH-].[K+].[O:3]1[CH2:6][C:5](=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4]1.[Br:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1>O1CCOCC1.[Cl-].[Na+].O>[Br:13][C:14]1[CH:19]=[C:18]([C:5]2([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][O:3][CH2:4]2)[CH:17]=[CH:16][CH:15]=1

참가 물질

6

반응물 3

HCID 14797Potassium HydroxideHCID 2734318(3-Bromophenyl)boronic acid2회HCID 53308471Ethyl 2-(oxetan-3-ylidene)acetate

생성물 1

HCID 57969689Ethyl 2-[3-(3-bromophenyl)oxetan-3-yl]acetate수율 71.3%

시약·촉매·용매 2

HCID 312751,4-Dioxane용매2회HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of [Rh(cod)C1]2 (171.3 mg, 0.3518 mmol) in 30 mL of dioxane was added aqueous KOH (6.097 mL of 1.5 M, 9.145 mmol) followed by ethyl 2-(oxetan-3-ylidene)acetate (1 g, 7.035 mmol) and a solution of (3-bromophenyl)boronic acid (2.119 g, 10.55 mmol) in 10 mL of dioxane. The reaction was stirred for 30 minutes at room temperature then further (3-bromophenyl)boronic acid (706 mg, 0.5 eq) was added and the reaction stirred overnight. Brine was added and the aqueous layer extracted twice with ethyl acetate. The combined organics were washed with brine and then dried, filtered and concentrated under reduced pressure. The crude product was purified on silica (Companion, 80 g) eluting with 1-20% EtOAc:Petrol ether to give ethyl 2-[3-(3-bromophenyl)oxetan-3-yl]acetate as a yellow oil (1.50 g, 71%).

후처리

  1. stirringthe reaction stirred overnight
  2. extractionthe aqueous layer extracted twice with ethyl acetate
  3. washThe combined organics were washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified on silica (Companion, 80 g)
  8. washeluting with 1-20% EtOAc

출처 및 근거

ORD 기록
ord-4440f4e92bb444bba2e696875d2d0acf
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367697B2

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