Hydrochloric Acid → 4-(3,5-Di-tert-butylphenyl)-2-cyclopropyl indene

HRID 923730노트

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HRID 923730 반응식
Br[C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[C:8]([C:11]1[CH:16]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:14]=[C:13]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:12]=1)[CH:7]=[CH:6][CH:5]=2.[CH:25]1([Mg]Br)[CH2:27][CH2:26]1.O1CCCC1.Cl>C1(C)C=CC=CC=1>[CH:25]1([C:2]2[CH2:3][C:4]3[C:9]([CH:10]=2)=[C:8]([C:11]2[CH:12]=[C:13]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:14]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:16]=2)[CH:7]=[CH:6][CH:5]=3)[CH2:27][CH2:26]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 1178183262-Bromo-4-(3,5-di-tert-butylphenyl)-1H-indeneHCID 178418630HCID 178418630, 화합물

생성물 1

HCID 1238090164-(3,5-Di-tert-butylphenyl)-2-cyclopropyl indene수율 48%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
60 °C

실험 절차

A solution of compound 6 (16.1 g, 42.0 mmol, 1 equiv) and anhydrous toluene (200 mL) was treated with [1,1′-bis(diphenylphos-phino)ferrocene]dichlopalladium(II) DCM adduct (3.43 g, 4.2 mmol, 0.1 equiv). After stirring for 10 minutes, 0.5 M cyclopropylmagnesium bromide in tetrahydrofuran (420 mL, 210 mmol, 5 equiv) was added dropwise. The reaction was heated at 60° C. overnight. The reaction was cooled with an ice bath, acidified with 1N HCl to pH 3 and extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with saturated brine (800 mL), dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified on an AnaLogix (65-200 g) column with dry-loading, eluting with heptanes to give compound 7 (7.0 g, 48% yield) as a white solid.

후처리

  1. temperatureThe reaction was cooled with an ice bath
  2. extractionextracted with ethyl acetate (3×500 mL)
  3. washThe combined organic layers were washed with saturated brine (800 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified on an AnaLogix (65-200 g) column
  7. customwith dry-loading
  8. washeluting with heptanes

출처 및 근거

ORD 기록
ord-ee36ac519c67450ebb7a1db6ea0c4e34
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09279024B2

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