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Iodoethane → Ethyl 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate

HRID 2275718
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HRID 2275718 반응식
[CH3:1][C:2]1([CH3:19])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[C:11]([CH2:15][C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[O:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:27][CH3:28]>CN(C=O)C.[Cl-].[Na+].O>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:19])([CH3:1])[O:3][B:4]([C:9]2[CH:10]=[C:11]([CH2:15][C:16]([O:18][CH2:27][CH3:28])=[O:17])[CH:12]=[CH:13][CH:14]=2)[O:5]1
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참가 물질

6

반응물 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 35832052-(3-(Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid

생성물 1

HCID 53217140Ethyl 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate수율 65%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 57417360
Sodium chloride; water
용매

실험 절차

To 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid (0.50 g, 1.91 mmol) in 20 mls of dry DMF was added cesium carbonate (1.24 g, 3.82 mmole) and iodoethane (0.20 mls, 2.48 mmol). This mixture was stirred at room temperature for 16 hours, then diluted with brine, extracted twice with EtOAc, extracts washed with brine (2×), dried over sodium sulfate and concentrated under reduced pressure to give 360 mgs (65%) of ethyl 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate as a clear oil.

후처리

  1. extractionextracted twice with EtOAc
  2. washextracts washed with brine (2×)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d8dc268ff5404ea196a37896c424046f
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09126940B2

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