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Chloroacetone → 4-Methyl-3-(2-oxo-propylsulfanyl)-benzoic acid ethyl ester

HRID 1466840
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HRID 1466840 반응식
[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([S:12][Si](C(C)C)(C(C)C)C(C)C)[CH:6]=1)[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(N(CC)CC)C.Cl[CH2:50][C:51](=[O:53])[CH3:52]>C1COCC1>[CH2:1]([O:3][C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([S:12][CH2:50][C:51](=[O:53])[CH3:52])[CH:6]=1)[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6571ChloroacetoneHCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 667648104-Methyl-3-triisopropylsilanylsulfanyl-benzoic acid ethyl ester

생성물 1

HCID 667651894-Methyl-3-(2-oxo-propylsulfanyl)-benzoic acid ethyl ester

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

To a stirred solution of 4-Methyl-3-triisopropylsilanylsulfanyl-benzoic acid ethyl ester (crude from step 1) in THF (50 mL) at 0° C. was added TBAF (13.9 mmol, 13.9 mL of a 1.0 M solution in THF). After 25 minutes, triethylamine (34.7 mmol, 4.74 mL) was added, followed by chloroacetone (16.7 mmol, 1.33 mL). The reaction was stirred for an additional 5 minutes, then subjected to standard aqueous workup. The crude material was purified by silica gel chromatography (0-50% EtOAc in hexanes) to afford the title compound.

후처리

  1. customThe crude material was purified by silica gel chromatography (0-50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-5f8d441c6cb4414dbe1c94319b3b8cd0
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09000025B2

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