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Ethyl Acetate → Methyl 4-tert-butyl-3-(prop-1-en-2-yl)benzoate

HRID 2235593
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HRID 2235593 반응식
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]([CH3:15])([CH3:14])[CH3:13])[C:5]([O:7][CH3:8])=[O:6].[C:16](B1OC(C)(C)C(C)(C)O1)([CH3:18])=[CH2:17].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>C1(C)C=CC=CC=1.[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:12]([C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[C:16]([CH3:18])=[CH2:17])([CH3:15])([CH3:14])[CH3:13]
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참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 11959028Methyl 3-bromo-4-(tert-butyl)benzoate

생성물 1

HCID 59300653Methyl 4-tert-butyl-3-(prop-1-en-2-yl)benzoate수율 88%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 1140Toluene용매
HCID 57417360Sodium chloride; water용매

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온도
100 °C

실험 절차

Methyl 3-bromo-4-tert-butylbenzoate (500 mg, 1.80 mmol, prepared according to the procedure of Hambley T. W. et al. Aust. J. Chem., 1990, 43, 807-814) and commercially available isopropenylboronic acid pinacol ester (0.693 mL, 3.6 mmol) were suspended in toluene (7 mL). Potassium carbonate (765 mg, 5.5 mmol) was added followed by Pd(PPh3)4 (213 mg, 0.180 mmol). The resulting mixture was heated to 100° C. and stirred for 24 hours. After cooling to room temperature, the mixture was treated with EtOAc (5 mL) and brine (5 mL). The organic layer was separated, washed twice with brine, dried with MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (0-10% EtOAc/hexane) to give 26.2 (378 mg, 88%) as a clear oil.

후처리

  1. temperatureAfter cooling to room temperature
  2. customThe organic layer was separated
  3. washwashed twice with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (0-10% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-22ab0369a2e74493a1ddcccfa469abd2
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07714008B2

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