Sodium hydride → 4-Methyl-3-triisopropylsilanylsulfanyl-benzoic acid ethyl ester

HRID 1466839

반응식

HRID 1466839 반응식
[CH:1]([Si:4]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[SH:5])([CH3:3])[CH3:2].[H-].[Na+].Br[C:15]1[CH:16]=[C:17]([CH:23]=[CH:24][C:25]=1[CH3:26])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C1COCC1.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>[CH2:21]([O:20][C:18](=[O:19])[C:17]1[CH:23]=[CH:24][C:25]([CH3:26])=[C:15]([S:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:6]([CH3:8])[CH3:7])[CH:9]([CH3:11])[CH3:10])[CH:16]=1)[CH3:22]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 3435097Tris(propan-2-yl)silanethiolHCID 14945865Ethyl 3-bromo-4-methylbenzoate

생성물 1

HCID 667648104-Methyl-3-triisopropylsilanylsulfanyl-benzoic acid ethyl ester

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a 0° C. stirred solution of triisopropylsilanethiol (14.28 mmol, 3.07 mL) in THF was added sodium hydride (14.28 mmol, 0.57 g of a 60 wt % dispersion in mineral oil). After 30 min, the mixture was added to a solution of ethyl 3-bromo-4-methylbenzoate (10.99 mmol, 2.67 g) at room temperature, followed by tetrakis(triphenylphosphine)palladium(0) (0.55 mmol, 0.64 g). The resulting mixture was warmed to reflux and stirred for 18 hours, then cooled to room temperature and subjected to standard aqueous workup to afford the title compound which was used crude in the next step.

후처리

  1. temperatureThe resulting mixture was warmed
  2. temperatureto reflux

출처 및 근거

ORD 기록
ord-75ea47a9512449939a7d3f0375b27f6f
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000025B2

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