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Potassium Hydroxide → Tert-butyl 3-(3-bromophenyl)-3-(2-ethoxy-2-oxoethyl)azetidine-1-carboxylate

HRID 384062
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HRID 384062 반응식
[OH-].[K+].[Br:3][C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1.[CH2:13]([O:15][C:16](=[O:29])[CH:17]=[C:18]1[CH2:21][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:19]1)[CH3:14]>O1CCOCC1.[Cl-].[Na+].O>[Br:3][C:4]1[CH:5]=[C:6]([C:18]2([CH2:17][C:16]([O:15][CH2:13][CH3:14])=[O:29])[CH2:19][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21]2)[CH:7]=[CH:8][CH:9]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 14797Potassium HydroxideHCID 2734318(3-Bromophenyl)boronic acidHCID 44195530tert-Butyl 3-(2-ethoxy-2-oxoethylidene)azetidine-1-carboxylate

생성물 1

HCID 57969607Tert-butyl 3-(3-bromophenyl)-3-(2-ethoxy-2-oxoethyl)azetidine-1-carboxylate수율 79%

시약·촉매·용매 2

HCID 312751,4-Dioxane용매2회
HCID 57417360
Sodium chloride; water
용매

실험 절차

To a solution of [RhCl(COD)]2 (63 mg, 0.031 mmol) in dioxane (10 mL) was added aqueous KOH (1.5M, 8.29 mmol, 5.53 mL), followed by (3-bromophenyl)boronic acid (1.67 g, 8.29 mmol). Then a solution of the tert-butyl 3-(2-ethoxy-2-oxoethylidene)azetidine-1-carboxylate in dioxane (7.5 mL) was added. The reaction mixture was microwaved at 100° C. for 5 min at 300 W. Brine was added and the mixture was extracted twice with ethyl acetate. The combined organics were washed with brine and then dried (MgSO4), filtered and concentrated. Purification by column chromatography (4/1 Pet ether/ethyl acetate) gave the Michael adduct (1.31 g, 79%) as a light yellow oil.

후처리

  1. customThe reaction mixture was microwaved at 100° C. for 5 min at 300 W
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. washThe combined organics were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography (4/1 Pet ether/ethyl acetate)

출처 및 근거

ORD 기록
ord-bf62d6c7c30f48cfb84a527de268c497
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08367697B2

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