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

HRID 2235593
ノート
印刷プレビュー

反応式

HRID 2235593 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 1140Toluene溶媒
HCID 57417360Sodium chloride; water溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-22ab0369a2e74493a1ddcccfa469abd2
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07714008B2

反応ノート

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